{"id":19882,"date":"2018-07-25T06:45:13","date_gmt":"2018-07-24T22:45:13","guid":{"rendered":"\/\/www.gsbet888.com\/?p=19882"},"modified":"2019-08-02T18:51:23","modified_gmt":"2019-08-02T10:51:23","slug":"%e5%8f%94%e4%b8%81%e6%b0%a7%e5%9f%ba%e7%be%b0%e5%9f%ba%e4%bf%9d%e6%8a%a4%e5%9f%ba-boc-protecting-group","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2018\/07\/%e5%8f%94%e4%b8%81%e6%b0%a7%e5%9f%ba%e7%be%b0%e5%9f%ba%e4%bf%9d%e6%8a%a4%e5%9f%ba-boc-protecting-group.html","title":{"rendered":"\u53d4\u4e01\u6c27\u57fa\u7fb0\u57fa\u4fdd\u62a4\u57fa Boc Protecting Group"},"content":{"rendered":"<h4>\u6982\u8981<\/h4>\n<p><strong>\u53d4\u4e01\u6c27\u57fa\u7fb0\u57fa\u4fdd\u62a4\u57fa\uff08<em>tert<\/em>-butoxycarbonyl, Boc\uff09<\/strong>\u3001\u5b83\u7ecf\u5e38\u7528\u4e8e\u901a\u8fc7\u5f62\u6210\u6c28\u57fa\u7532\u9178\u916f\u6765\u4fdd\u62a4\u80fa\u57fa\u3002\u7279\u522b\u662f\uff0c\u5b83\u88ab\u7528\u4f5c\u80fa\u4fdd\u62a4\u57fa\u7684\u4e3b\u8981\u9009\u62e9\u3002\u5728\u67d0\u4e9b\u60c5\u51b5\u4e0b\uff0c\u5b83\u8fd8\u7528\u4e8e\u9152\u7cbe\u548c\u82ef\u915a\u4e0a\u7f9f\u57fa\u7684\u4fdd\u62a4\u57fa\u3002<\/p>\n<p>\u5bf9\u4e8e\u5f3a\u78b1\u6761\u4ef6\u4e0b\u7684\u916f\u6c34\u89e3\u6761\u4ef6\u30fb\u4eb2\u6838\u6761\u4ef6\u30fb\u63a5\u89e6\u8fd8\u539f\u6761\u4ef6\u30fb\u5f31\u7684\u6c22\u5316\u7269\u7684\u8fd8\u539f\u6761\u4ef6\u8010\u53d7\u6027\u597d\uff0c\u8131\u4fdd\u62a4\u901a\u5e38\u5728\u5f3a\u9178\u6027\u6761\u4ef6\u4e0b\u8fdb\u884c\u3002\u56e0\u6b64\uff0c\u5b83\u53ef\u4ee5\u4e0eFmoc\u4fdd\u62a4\u57fa\uff0cCbz\u4fdd\u62a4\u57fa\u7b49\u4e92\u8865\u4f7f\u7528\u3002<\/p>\n<p>\u5b83\u8fd8\u5e7f\u6cdb\u7528\u4e8e\u80bd\u56fa\u76f8\u5408\u6210\u65b9\u6cd5\u3002<br \/>\n<span id=\"more-58886\"><\/span><\/p>\n<h4>\u57fa\u672c\u6587\u732e<\/h4>\n<ul>\n<li>Lundt, B. F.; Johansen, N. L.; V\u00f8lund, A.; Markussen, J.<em> Int. J. Pept. Protein Res.<\/em><strong>1978<\/strong>, <em>12<\/em>, 258. doi:<a href=\"http:\/\/dx.doi.org\/10.1111\/j.1399-3011.1978.tb02896.x\">10.1111\/j.1399-3011.1978.tb02896.x<\/a><\/li>\n<li>Chankeshwara, S. V.; Chakraborti, A. K. <em>Org. Lett.<\/em> <strong>2006<\/strong>, <em>8<\/em>, 3259. doi:<a href=\"http:\/\/dx.doi.org\/10.1021\/ol0611191\">10.1021\/ol0611191<\/a><\/li>\n<\/ul>\n<h5>Boc-SPPS<\/h5>\n<ul>\n<li>Merrifield, R. B. <em>Biochemistry<\/em> <strong>1964<\/strong>, <em>3<\/em>, 1385. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/bi00897a032\">10.1021\/bi00897a032<\/a><\/li>\n<\/ul>\n<h5>review<\/h5>\n<ul>\n<li>Agami, C.; Couty, F. <em>Tetrahedron<\/em> <strong>2002<\/strong>, <em>58<\/em>, 2701. doi:<a href=\"http:\/\/dx.doi.org\/10.1016\/S0040-4020(02)00131-X\">10.1016\/S0040-4020(02)00131-X<\/a><\/li>\n<\/ul>\n<h4>\u53cd\u5e94\u673a\u7406<\/h4>\n<h5>\u4fdd\u62a4<\/h5>\n<p><strong>\u4e8c\u78b3\u9178\u4e8c\u53d4\u4e01\u916f\uff08Boc<sub>2<\/sub>O\uff09<\/strong>\u662f\u7528\u7684\u6700\u591a\u7684\u3002\u53cd\u5e94\u4e2d\u7684\u78b1\u901a\u5e38\u4e3a\u5421\u5576\u6216\u4e09\u4e59\u80fa\u3002\u5bf9\u4e8e\u6c28\u57fa\u9178\u7684\u4fdd\u62a4\u7b49\uff0c\u4f7f\u7528\u65e0\u673a\u78b1\u7684Schotten-Baumann\u6761\u4ef6\u4e5f\u5f88\u5e38\u89c1\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19884 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_6-680x140.png\" alt=\"\" width=\"544\" height=\"112\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_6-680x140.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_6-300x62.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_6.png 768w\" sizes=\"(max-width: 544px) 100vw, 544px\" \/><\/p>\n<h5>\u8131\u4fdd\u62a4<\/h5>\n<p>\u5728\u5f3a\u9178\u6027\u6761\u4ef6\u4e0b\u901a\u8fc7\u4ea7\u751f\u53d4\u4e01\u57fa\u9633\u79bb\u5b50\u8131\u4fdd\u62a4\u3002\u7ecf\u5e38\u4f7f\u7528\u4e09\u6c1f\u4e59\u9178\uff08TFA\uff09\/\u4e8c\u6c2f\u7532\u70f7\u6216neat\u6761\u4ef6\uff0c\u76d0\u9178\/\u7532\u9187\u6761\u4ef6\u7b49\u3002\u7531\u4e8e\u4ec5\u526f\u4ea7\u6325\u53d1\u6027\u5f02\u4e01\u70ef\u548cCO<sub>2<\/sub>\uff0c\u56e0\u6b64\u540e\u5904\u7406\u4e5f\u5f88\u7b80\u5355\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19885 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_7-680x189.png\" alt=\"\" width=\"651\" height=\"181\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_7-680x189.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_7-300x83.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_7.png 768w\" sizes=\"(max-width: 651px) 100vw, 651px\" \/><\/p>\n<h4>\u53cd\u5e94\u5b9e\u4f8b<\/h4>\n<p>\u901a\u8fc7\u6dfb\u52a0DMAP\u3001\u53ef\u4ee5\u5bf9\u4eb2\u6838\u6027\u8f83\u4f4e\u7684\u9170\u80fa\u57fa\u4fdd\u62a4\u3001\u800c\u4e14\u53ef\u4ee5\u8fdb\u884c\u5432\u54da\u4e0a\u6c2e\u7684\u4fdd\u62a4\u6216\u8005\u4e5f\u53ef\u4ee5\u5408\u6210di-Boc\u4f53\u3002\u4e0b\u9762\u4e3a\u5176\u4e2d\u7684\u4e00\u4e2a\u793a\u4f8b[1]\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19886 size-large\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_5-680x167.png\" alt=\"\" width=\"680\" height=\"167\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_5-680x167.png 680w, 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\/><\/p>\n<p>\u5bf9\u73af\u72b6\u6c28\u57fa\u7532\u9178\u916f\u548c\u6076\u5511\u70f7\u916e\u7684\u7fb0\u57fa\u8fdb\u884c\u52a0\u6eb6\u5242\u5206\u89e3\u65f6\uff0c\u53ef\u4ee5\u7528Boc\u4fdd\u62a4[3]\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19888 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_9.png\" alt=\"\" width=\"432\" height=\"112\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_9.png 355w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_9-300x78.png 300w\" sizes=\"(max-width: 432px) 100vw, 432px\" \/><\/p>\n<p>one-step\u5c06Fmoc\u57fa\u66ff\u6362\u6210Boc\u57fa[4]\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19889 size-large\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_10-680x135.png\" alt=\"\" width=\"680\" height=\"135\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_10-680x135.png 680w, 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\/><\/p>\n<p>TMSOTf\/Et<sub>3<\/sub>N\u6216\u8005TMSOTf\/2,6-lutidine\u6761\u4ef6\u4e0b\u3001\u53ef\u4ee5\u8fdb\u884c\u5bf9\u9178\u6027\u6761\u4ef6\u4e0d\u7a33\u5b9a\u7684\u5316\u5408\u7269\u7684\u9009\u62e9\u6027\u8131Boc\u53cd\u5e94\u3002\u4e0b\u9762\u5c31\u662f\u4e00\u4e2aCyclotheonamide B\u7684\u5168\u5408\u6210\u7684\u5b9e\u7528\u4f8b\u5b50[6]\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19891 size-large\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_12-680x246.png\" alt=\"\" width=\"680\" height=\"246\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_12-680x246.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_12-300x109.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_12.png 768w\" sizes=\"(max-width: 680px) 100vw, 680px\" \/><\/p>\n<p>TMS-I\u6761\u4ef6\u4e0b\u7684\u8131\u4fdd\u62a4[7]\u3002\u4e0b\u8ff0\u7684\u5b9e\u4f8b\u4e2d[8]\u3001\u5bf9\u4e8e\u5e95\u7269\u4e2d\u542b\u6709\u5176\u4ed6\u654f\u611f\u57fa\u56e2\u7684\u60c5\u51b5\u4e0b\uff0c\u4e5f\u53ef\u4ee5\u5b9e\u73b0\u9009\u62e9\u6027\u8131Boc\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19892 size-large\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_4-680x255.png\" alt=\"\" width=\"680\" height=\"255\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_4-680x255.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_4-300x113.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_4.png 768w\" sizes=\"(max-width: 680px) 100vw, 680px\" \/><\/p>\n<p>\u53e6\u5916\u901a\u8fc7LiAlH<sub>4<\/sub>\u5904\u7406\u3001\u76f4\u63a5\u8fd8\u539f\u6210\u7532\u57fa\u7684\u60c5\u51b5\u4e5f\u6709\u3002\u8bf7\u53c2\u7167\u4e0b\u56fe\u4e2d(+)-Esermethole\u5408\u6210\u5e94\u7528\u5b9e\u4f8b[9]\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19893 size-large\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_13-680x210.png\" alt=\"\" width=\"680\" height=\"210\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_13-680x210.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_13-300x93.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_13.png 768w\" sizes=\"(max-width: 680px) 100vw, 680px\" \/><\/p>\n<h4>\u5b9e\u9a8c\u6280\u5de7<\/h4>\n<ul>\n<li>\u5728\u8131\u4fdd\u62a4\u8fc7\u7a0b\u4e2d\uff0c\u5316\u5408\u7269\u4e2d\u542b\u6709\u7684\u4eb2\u6838\u90e8\u5206\u901a\u5e38\u4e0e\u526f\u4ea7\u7684\u53d4\u4e01\u57fa\u9633\u79bb\u5b50\u53cd\u5e94\u3002\u4e3a\u4e86\u9632\u6b62\u8fd9\u79cd\u60c5\u51b5\uff0c\u53ef\u4ee5\u52a0\u5165\u9633\u79bb\u5b50\u6e05\u9664\u5242\uff08\u82ef\u7532\u919a\uff0c\u786b\u4ee3\u82ef\u7532\u919a\uff0c\u82ef\u786b\u915a\uff0c\u4e8c\u7532\u57fa\u786b\u919a\u7b49\uff09\u4f5c\u4e3a\u6dfb\u52a0\u5242\u3002<\/li>\n<li>\u5728Boc\u8131\u4fdd\u62a4\u8fc7\u7a0b\u4e2d\u5f62\u6210\u7684\u94f5\u5316\u5408\u7269\u662f\u3001\u53ef\u4ee5\u901a\u8fc72%MeOH\/Et<sub>2<\/sub>O\u4ece\u6709\u673a\u5316\u5408\u7269\u4e2d\u5206\u79bb\uff08<a href=\"https:\/\/chemtips.wordpress.com\/2013\/02\/26\/shake-and-drain\/\">\u53c2\u8003<\/a>\uff09\u3002<\/li>\n<li>\u54aa\u5511\/\u4e09\u6c1f\u4e59\u9187\u6761\u4ef6\u9002\u5408\u4e8e\u7834\u574f\u548c\u9664\u53bb\u8fc7\u91cf\u7684Boc<sub>2<\/sub>O[10]\u3002<\/li>\n<\/ul>\n<h4>\u5b9e\u9a8c\u6b65\u9aa4<\/h4>\n<ul>\n<li><a href=\"http:\/\/cssp.chemspider.com\/611\">Boc\u4fdd\u62a4\u82ef\u57fa\u7518\u6c28\u9178<\/a><\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19894 size-large\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_2-680x173.png\" alt=\"\" width=\"680\" height=\"173\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_2-680x173.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_2-300x76.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_2.png 768w\" sizes=\"(max-width: 680px) 100vw, 680px\" \/><\/p>\n<p>(<em>R<\/em>)-\u82ef\u57fa\u7518\u6c28\u9178\uff081.0 g\u30017.3 mmol\uff09\u6eb6\u89e3\u4e8eTHF\uff0810 mL\uff09\u3001\u5728\u51b0\u6d74\u4e0b\u52a0\u5165\u4e09\u4e59\u80fa\uff082.14 mL\u300115.4 mmol\uff09\u548cBoc<sub>2<\/sub>O\uff081.08 g\u30017.7 mmol\uff09\u7684THF\u6eb6\u6db2\uff0810 mL\uff09\u3001\u5728\u5ba4\u6e29\u4e0b\u6405\u62cc2\u5c0f\u65f6\u3002 \u7136\u540e\u51cf\u538b\u6d53\u7f29\u5230\u4e00\u534a\u4f53\u79ef\uff0c\u7136\u540e\u52a0\u5165hexane\u91cd\u7ed3\u6676\u3002 \u62bd\u6ee4\u5f97\u5230\u56fa\u4f53\u3001\u7528hexane\u6d17\u51c0\u3002 \u4ea7\u73871.72 g\uff0899\uff05\uff09\u3002<\/p>\n<ul>\n<li><a href=\"http:\/\/cssp.chemspider.com\/Article.aspx?id=608\">\u4f7f\u7528\u76d0\u9178\/\u4e8c\u6076\u70f7\u6eb6\u6db2\u8fdb\u884cBoc\u8131\u4fdd\u62a4<\/a><\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-19895 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_3.png\" alt=\"\" width=\"379\" height=\"99\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_3.png 379w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/07\/Boc_3-300x78.png 300w\" sizes=\"(max-width: 379px) 100vw, 379px\" \/><\/p>\n<p>\u5728\u4e8c\u6c27\u516d\u73af\uff0810 mL\uff09\u4e2d\u3001\uff08<em>R<\/em>\uff09&#8211;2-\uff08\u53d4\u4e01\u6c27\u57fa\u7fb0\u57fa\u6c28\u57fa\uff09-2-\u82ef\u57fa\u4e59\u57fa\u7532\u78fa\u9178\u76d0\uff082.5 g\u30017.9 mmol\uff09\u7684\u6eb6\u6db2\u4e2d\u6ef4\u52a0HCl\uff0810 mL\u30014 M in dioxane\uff09\u3001\u6405\u62cc1\u5c0f\u65f6\u3002\u65cb\u84b8\u9664\u53bb\u6325\u53d1\u6027\u7269\u8d28\uff0cresidue\u7528\u4e59\u8148\/\u4e59\u919a\u91cd\u7ed3\u6676\u3002 \u4ea7\u73871.28 g\uff0865\uff05\uff09<\/p>\n<h4>\u53c2\u8003\u6587\u732e<\/h4>\n<ol>\n<li>Englund, E. A.; Gopi, H. N.; Appella, D. H. <em>Org. Lett.<\/em> <strong>2004<\/strong>, <em>6<\/em>, 213. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/ol0361599\">10.1021\/ol0361599<\/a><\/li>\n<li>(a) Basel, Y.; Hassner, A. <em>J. Org. Chem.<\/em> <strong>2000<\/strong>, <em>65<\/em>, 6368. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/jo000257f\">10.1021\/jo000257f<\/a>(b) Ragnarsson, U.; Grehn, L. <em>Acc. Chem. Res.<\/em> <strong>1998<\/strong>, <em>31<\/em>, 494. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/ar980001k\">10.1021\/ar980001k<\/a><\/li>\n<li>Ishizuka, T.; Kunieda, T. <em>Tetrahedron Lett.<\/em> <strong>1987<\/strong>, <em>28<\/em>, 4185. doi:<a href=\"http:\/\/dx.doi.org\/10.1016\/S0040-4039(00)95574-6\">10.1016\/S0040-4039(00)95574-6<\/a><\/li>\n<li>Li, W.-R.; Jiang, J.; Joullie, M. M. <em>Tetrahedron Lett.<\/em> <strong>1993<\/strong>, <em>34<\/em>, 1413. doi:<a href=\"http:\/\/dx.doi.org\/10.1016\/S0040-4039(00)60305-2\">10.1016\/S0040-4039(00)60305-2<\/a><\/li>\n<li>Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. <em>Tetrahedron Lett.<\/em> <strong>1989<\/strong>, <em>30<\/em>, 837. doi:<a href=\"http:\/\/dx.doi.org\/10.1016\/S0040-4039(01)80629-8\">10.1016\/S0040-4039(01)80629-8<\/a><\/li>\n<li>Bastiaans, H. M. M.; van de Baan, J. L.; Ottenheijm, H. C. J. <em>J. Org. Chem.<\/em> <strong>1997<\/strong>, <em>62<\/em>, 3880. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/jo961447m\">10.1021\/jo961447m<\/a><\/li>\n<li>(a) Lott, R. S.; Chauhan, V. S.; Stammer, C. H. <em>J. Chem. Soc., Chem. Commun.<\/em><strong>1979<\/strong>, 495. doi:<a href=\"http:\/\/dx.doi.org\/10.1039\/C39790000495\">10.1039\/C39790000495<\/a> (b) Olah, G.; Narang, S. C. <em>Tetrahedron<\/em><strong>1982<\/strong>, <em>38<\/em>, 2225. doi:<a href=\"http:\/\/dx.doi.org\/10.1016\/0040-4020(82)87002-6\">10.1016\/0040-4020(82)87002-6<\/a> (c) Jung, M. E.; Lyster, M. A. <em>J. Chem. Soc., Chem. Commun.<\/em> <strong>1978<\/strong>, 315. doi:<a href=\"http:\/\/dx.doi.org\/10.1039\/C39780000315\">10.1039\/C39780000315<\/a><\/li>\n<li>Liu, Z.; Yasuda, N.; Simeone, M.; Reamer, R. A. <em>J. Org. Chem.<\/em> <strong>2014<\/strong>, <em>79<\/em>, 11792. doi:<a href=\"http:\/\/dx.doi.org\/10.1021\/jo502319z\">10.1021\/jo502319z<\/a><\/li>\n<li>Bui, T.; Syed, S.; Barbas, C. F. III <em>J. Am. Chem. Soc.<\/em> <strong>2009<\/strong>, <em>131<\/em>, 8758. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/ja903520c\">10.1021\/ja903520c<\/a><\/li>\n<li>Basel, Y.; Hassner, A. <em>Synthesis<\/em> <strong>2001<\/strong>, 550. DOI: <a href=\"http:\/\/dx.doi.org\/10.1055\/s-2001-12350\">10.1055\/s-2001-12350<\/a><\/li>\n<\/ol>\n<h4>\u76f8\u5173\u4e66\u7c4d<\/h4>\n<div class=\"amazonjs_item amazonjs_book\">\n<div class=\"amazonjs_image\"><a class=\"amazonjs_link\" title=\"Greene's Protective Groups in Organic Synthesis\" href=\"https:\/\/www.amazon.co.jp\/Greenes-Protective-Groups-Organic-Synthesis\/dp\/1118057481?SubscriptionId=AKIAI6Q3RDQBU2J6P3JQ&amp;tag=chemstation-22&amp;linkCode=xm2&amp;camp=2025&amp;creative=165953&amp;creativeASIN=1118057481\" target=\"_blank\" rel=\"noopener\" data-role=\"amazonjs_product\" data-asin=\"1118057481\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/images-fe.ssl-images-amazon.com\/images\/I\/41wPq6PXD3L._SL160_.jpg\" alt=\"Greene's Protective Groups in Organic Synthesis\" width=\"107\" height=\"160\" \/><\/a><\/div>\n<div class=\"amazonjs_info\">\n<h4><a class=\"amazonjs_link\" title=\"Greene's Protective Groups in Organic Synthesis\" href=\"https:\/\/www.amazon.co.jp\/Greenes-Protective-Groups-Organic-Synthesis\/dp\/1118057481?SubscriptionId=AKIAI6Q3RDQBU2J6P3JQ&amp;tag=chemstation-22&amp;linkCode=xm2&amp;camp=2025&amp;creative=165953&amp;creativeASIN=1118057481\" target=\"_blank\" rel=\"noopener\" data-role=\"amazonjs_product\" data-asin=\"1118057481\">Greene&#8217;s Protective Groups in Organic Synthesis<\/a><\/h4>\n<ul>\n<li><b>\u8457\u8005<\/b>Peter G. 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Wuts<\/li>\n<li class=\"amazonjs_price\" title=\"\u4fa1\u683c\u304a\u3088\u3073\u767a\u9001\u53ef\u80fd\u6642\u671f\u306f\u8868\u793a\u3055\u308c\u305f\u65e5\u4ed8\/\u6642\u523b\u306e\u6642\u70b9\u306e\u3082\u306e\u3067\u3042\u308a\u3001\u5909\u66f4\u3055\u308c\u308b\u5834\u5408\u304c\u3042\u308a\u307e\u3059\u3002\u5546\u54c1\u306e\u8ca9\u58f2\u306b\u304a\u3044\u3066\u306f\u3001\u8cfc\u5165\u306e\u6642\u70b9\u3067 [Amazon.co.jp \u307e\u305f\u306f Javari.jp] \u306b\u8868\u793a\u3055\u308c\u3066\u3044\u308b\u4fa1\u683c\u304a\u3088\u3073\u767a\u9001\u53ef\u80fd\u6642\u671f\u306e\u60c5\u5831\u304c\u9069\u7528\u3055\u308c\u307e\u3059\u3002\"><b>\u53c2\u8003\u4fa1\u683c<\/b><span class=\"amazonjs_listprice\">\uffe5 12,342<\/span><br \/>\n<b><\/b><\/li>\n<li><b>\u51fa\u7248\u793e<\/b>John Wiley &amp; Sons Inc<\/li>\n<\/ul>\n<\/div>\n<p><a class=\"amazonjs_review\" title=\"Greene's Protective Groups in Organic Synthesis \u30ab\u30b9\u30bf\u30de\u30fc\u30ec\u30d3\u30e5\u30fc\" href=\"https:\/\/www.amazon.jp\/reviews\/iframe?akid=AKIAI6Q3RDQBU2J6P3JQ&amp;alinkCode=xm2&amp;asin=1118057481&amp;atag=chemstation-22&amp;exp=2018-07-24T02%3A17%3A19Z&amp;v=2&amp;sig=JivZq3ptDbRVlTDFJOnWkjLa1vYGyosWmwkXxZdGSGo%253D&amp;TB_iframe=true&amp;height=500&amp;width=600\" target=\"_blank\" rel=\"noopener\">\u30ab\u30b9\u30bf\u30de\u30fc\u30ec\u30d3\u30e5\u30fc\u3092\u898b\u308b<\/a><\/p>\n<div class=\"amazonjs_footer\"><\/div>\n<\/div>\n<h4>\u5916\u90e8\u94fe\u63a5<\/h4>\n<ul>\n<li><a href=\"https:\/\/en.wikipedia.org\/wiki\/Tert-Butyloxycarbonyl_protecting_group\"><em>tert<\/em>-Butyloxycarbonyl protecting group \u00a0\u2013 Wikipedia<\/a><\/li>\n<li><a href=\"https:\/\/www.organic-chemistry.org\/protectivegroups\/amino\/boc-amino.htm\"><em>tert<\/em>-butyl carbamate<\/a> (Organic Chemistry Portal)<\/li>\n<li><a href=\"https:\/\/www.ethz.ch\/content\/dam\/ethz\/special-interest\/chab\/organic-chemistry\/wennemers-dam\/documents\/Teaching_Peptide\/Peptides%202.pdf\">Protecting Group (PG)<\/a> (PDF)<\/li>\n<li><a href=\"http:\/\/www.chempep.com\/ChemPep-Boc-Solid-Phase-Peptide-Synthesis.htm#C1\">Boc solid phase peptide synthesis<\/a><\/li>\n<\/ul>\n<p>\u672c\u6587\u7248\u6743\u5c5e\u4e8e<strong>\u00a0<a href=\"\/\/www.gsbet888.com\/\">Chem-Station\u5316\u5b66\u7a7a\u95f4<\/a>\uff0c<\/strong>\u00a0\u6b22\u8fce\u70b9\u51fb\u6309\u94ae\u5206\u4eab\uff0c\u672a\u7ecf\u8bb8\u53ef\uff0c\u8c22\u7edd\u8f6c\u8f7d\uff01<\/p>\n","protected":false},"excerpt":{"rendered":"\u6982\u8981 \u53d4\u4e01\u6c27\u57fa\u7fb0\u57fa\u4fdd\u62a4\u57fa\uff08tert-butoxycarbonyl, Boc\uff09\u3001\u5b83\u7ecf\u5e38\u7528\u4e8e\u901a\u8fc7\u5f62\u6210\u6c28\u57fa\u7532\u9178\u916f\u6765\u4fdd\u62a4\u80fa\u57fa\u3002\u7279\u522b\u662f\uff0c\u5b83\u88ab\u7528\u4f5c\u80fa\u4fdd\u62a4\u57fa\u7684\u4e3b\u8981\u9009\u62e9\u3002\u5728\u67d0\u4e9b\u60c5\u51b5\u4e0b\uff0c\u5b83\u8fd8\u7528\u4e8e\u9152\u7cbe\u548c\u82ef\u915a\u4e0a\u7f9f\u57fa\u7684\u4fdd\u62a4\u57fa\u3002 \u5bf9\u4e8e\u5f3a\u78b1\u6761\u4ef6\u4e0b\u7684\u916f\u6c34\u89e3\u6761\u4ef6\u30fb\u4eb2\u6838\u6761\u4ef6\u30fb\u63a5\u89e6\u8fd8\u539f\u6761\u4ef6\u30fb\u5f31\u7684\u6c22\u5316\u7269\u7684\u8fd8\u539f\u6761\u4ef6\u8010\u53d7\u6027\u597d\uff0c\u8131\u4fdd\u62a4\u901a\u5e38\u5728\u5f3a\u9178\u6027\u6761\u4ef6\u4e0b\u8fdb\u884c\u3002\u56e0\u6b64\uff0c\u5b83\u53ef\u4ee5\u4e0eFmoc\u4fdd\u62a4\u57fa\uff0cCbz\u4fdd\u62a4\u57fa\u7b49\u4e92\u8865\u4f7f\u7528\u3002 \u5b83\u8fd8\u5e7f\u6cdb\u7528\u4e8e\u80bd\u56fa\u76f8\u5408\u6210\u65b9\u6cd5\u3002 \u57fa\u672c\u6587\u732e Lundt, B. F.; Johansen, N. L.; V\u00f8lund, A.; Markussen, J. Int. J. Pept. Protein Res.1978, 12, 258. doi:10.1111\/j.1399-3011.1978.tb02896.x Chankeshwara, S. V.; Chakraborti, A. K. Org. Lett. 2006, 8, 3259. doi:10.1021\/ol0611191 Boc-SPPS Merrifield, R. B. Biochemistry 1964, 3, 1385. DOI: 10.1021\/bi00897a032 review Agami, C.; Couty, F. Tetrahedron 2002, 58, 2701. doi:10.1016\/S0040-4020(02)00131-X \u53cd\u5e94\u673a\u7406 \u4fdd\u62a4 \u4e8c\u78b3\u9178\u4e8c\u53d4\u4e01\u916f\uff08Boc2O\uff09\u662f\u7528\u7684\u6700\u591a\u7684\u3002\u53cd\u5e94\u4e2d\u7684\u78b1\u901a\u5e38\u4e3a\u5421\u5576\u6216\u4e09\u4e59\u80fa\u3002\u5bf9\u4e8e\u6c28\u57fa\u9178\u7684\u4fdd\u62a4\u7b49\uff0c\u4f7f\u7528\u65e0\u673a\u78b1\u7684Schotten-Baumann\u6761\u4ef6\u4e5f\u5f88\u5e38\u89c1\u3002 \u8131\u4fdd\u62a4 \u5728\u5f3a\u9178\u6027\u6761\u4ef6\u4e0b\u901a\u8fc7\u4ea7\u751f\u53d4\u4e01\u57fa\u9633\u79bb\u5b50\u8131\u4fdd\u62a4\u3002\u7ecf\u5e38\u4f7f\u7528\u4e09\u6c1f\u4e59\u9178\uff08TFA\uff09\/\u4e8c\u6c2f\u7532\u70f7\u6216neat\u6761\u4ef6\uff0c\u76d0\u9178\/\u7532\u9187\u6761\u4ef6\u7b49\u3002\u7531\u4e8e\u4ec5\u526f\u4ea7\u6325\u53d1\u6027\u5f02\u4e01\u70ef\u548cCO2\uff0c\u56e0\u6b64\u540e\u5904\u7406\u4e5f\u5f88\u7b80\u5355\u3002 \u53cd\u5e94\u5b9e\u4f8b \u901a\u8fc7\u6dfb\u52a0DMAP\u3001\u53ef\u4ee5\u5bf9\u4eb2\u6838\u6027\u8f83\u4f4e\u7684\u9170\u80fa\u57fa\u4fdd\u62a4\u3001\u800c\u4e14\u53ef\u4ee5\u8fdb\u884c\u5432\u54da\u4e0a\u6c2e\u7684\u4fdd\u62a4\u6216\u8005\u4e5f\u53ef\u4ee5\u5408\u6210di-Boc\u4f53\u3002\u4e0b\u9762\u4e3a\u5176\u4e2d\u7684\u4e00\u4e2a\u793a\u4f8b[1]\u3002 DMAP\u6761\u4ef6\u4e0b\u4e5f\u4f1a\u5b58\u5728over reaction\u7684\u95ee\u9898\uff08\u7279\u522b\u662f\u82ef\u80fa\u7684\u4fdd\u62a4\u7b49\uff09\uff0c\u5728\u8fd9\u4e2a\u65f6\u5019\u3001\u53ef\u4ee5\u9009\u62e9\u8bd5\u4e00\u4e0bN-\u7532\u57fa\u54aa\u5511\u7684\u6761\u4ef6[2]\u3002 \u5bf9\u73af\u72b6\u6c28\u57fa\u7532\u9178\u916f\u548c\u6076\u5511\u70f7\u916e\u7684\u7fb0\u57fa\u8fdb\u884c\u52a0\u6eb6\u5242\u5206\u89e3\u65f6\uff0c\u53ef\u4ee5\u7528Boc\u4fdd\u62a4[3]\u3002 one-step\u5c06Fmoc\u57fa\u66ff\u6362\u6210Boc\u57fa[4]\u3002 \u53e0\u6c2e\u57fa\u5728\u52a0\u6c22\u8fd8\u539f\u7684\u6761\u4ef6\u4e0b\u4e0eBoc2O\u5171\u5b58\u3001\u5f97\u5230Boc\u4fdd\u62a4\u7684\u4ea7\u7269[5]\u3002 TMSOTf\/Et3N\u6216\u8005TMSOTf\/2,6-lutidine\u6761\u4ef6\u4e0b\u3001\u53ef\u4ee5\u8fdb\u884c\u5bf9\u9178\u6027\u6761\u4ef6\u4e0d\u7a33\u5b9a\u7684\u5316\u5408\u7269\u7684\u9009\u62e9\u6027\u8131Boc\u53cd\u5e94\u3002\u4e0b\u9762\u5c31\u662f\u4e00\u4e2aCyclotheonamide B\u7684\u5168\u5408\u6210\u7684\u5b9e\u7528\u4f8b\u5b50[6]\u3002 TMS-I\u6761\u4ef6\u4e0b\u7684\u8131\u4fdd\u62a4[7]\u3002\u4e0b\u8ff0\u7684\u5b9e\u4f8b\u4e2d[8]\u3001\u5bf9\u4e8e\u5e95\u7269\u4e2d\u542b\u6709\u5176\u4ed6\u654f\u611f\u57fa\u56e2\u7684\u60c5\u51b5\u4e0b\uff0c\u4e5f\u53ef\u4ee5\u5b9e\u73b0\u9009\u62e9\u6027\u8131Boc\u3002 \u53e6\u5916\u901a\u8fc7LiAlH4\u5904\u7406\u3001\u76f4\u63a5\u8fd8\u539f\u6210\u7532\u57fa\u7684\u60c5\u51b5\u4e5f\u6709\u3002\u8bf7\u53c2\u7167\u4e0b\u56fe\u4e2d(+)-Esermethole\u5408\u6210\u5e94\u7528\u5b9e\u4f8b[9]\u3002 \u5b9e\u9a8c\u6280\u5de7 \u5728\u8131\u4fdd\u62a4\u8fc7\u7a0b\u4e2d\uff0c\u5316\u5408\u7269\u4e2d\u542b\u6709\u7684\u4eb2\u6838\u90e8\u5206\u901a\u5e38\u4e0e\u526f\u4ea7\u7684\u53d4\u4e01\u57fa\u9633\u79bb\u5b50\u53cd\u5e94\u3002\u4e3a\u4e86\u9632\u6b62\u8fd9\u79cd\u60c5\u51b5\uff0c\u53ef\u4ee5\u52a0\u5165\u9633\u79bb\u5b50\u6e05\u9664\u5242\uff08\u82ef\u7532\u919a\uff0c\u786b\u4ee3\u82ef\u7532\u919a\uff0c\u82ef\u786b\u915a\uff0c\u4e8c\u7532\u57fa\u786b\u919a\u7b49\uff09\u4f5c\u4e3a\u6dfb\u52a0\u5242\u3002 \u5728Boc\u8131\u4fdd\u62a4\u8fc7\u7a0b\u4e2d\u5f62\u6210\u7684\u94f5\u5316\u5408\u7269\u662f\u3001\u53ef\u4ee5\u901a\u8fc72%MeOH\/Et2O\u4ece\u6709\u673a\u5316\u5408\u7269\u4e2d\u5206\u79bb\uff08\u53c2\u8003\uff09\u3002 \u54aa\u5511\/\u4e09\u6c1f\u4e59\u9187\u6761\u4ef6\u9002\u5408\u4e8e\u7834\u574f\u548c\u9664\u53bb\u8fc7\u91cf\u7684Boc2O[10]\u3002 \u5b9e\u9a8c\u6b65\u9aa4 Boc\u4fdd\u62a4\u82ef\u57fa\u7518\u6c28\u9178 (R)-\u82ef\u57fa\u7518\u6c28\u9178\uff081.0 g\u30017.3 mmol\uff09\u6eb6\u89e3\u4e8eTHF\uff0810 mL\uff09\u3001\u5728\u51b0\u6d74\u4e0b\u52a0\u5165\u4e09\u4e59\u80fa\uff082.14 mL\u300115.4 mmol\uff09\u548cBoc2O\uff081.08 g\u30017.7 mmol\uff09\u7684THF\u6eb6\u6db2\uff0810 mL\uff09\u3001\u5728\u5ba4\u6e29\u4e0b\u6405\u62cc2\u5c0f\u65f6\u3002 \u7136\u540e\u51cf\u538b\u6d53\u7f29\u5230\u4e00\u534a\u4f53\u79ef\uff0c\u7136\u540e\u52a0\u5165hexane\u91cd\u7ed3\u6676\u3002 \u62bd\u6ee4\u5f97\u5230\u56fa\u4f53\u3001\u7528hexane\u6d17\u51c0\u3002 \u4ea7\u73871.72 g\uff0899\uff05\uff09\u3002 \u4f7f\u7528\u76d0\u9178\/\u4e8c\u6076\u70f7\u6eb6\u6db2\u8fdb\u884cBoc\u8131\u4fdd\u62a4 \u5728\u4e8c\u6c27\u516d\u73af\uff0810 mL\uff09\u4e2d\u3001\uff08R\uff09&#8211;2-\uff08\u53d4\u4e01\u6c27\u57fa\u7fb0\u57fa\u6c28\u57fa\uff09-2-\u82ef\u57fa\u4e59\u57fa\u7532\u78fa\u9178\u76d0\uff082.5 g\u30017.9 mmol\uff09\u7684\u6eb6\u6db2\u4e2d\u6ef4\u52a0HCl\uff0810 mL\u30014 M in dioxane\uff09\u3001\u6405\u62cc1\u5c0f\u65f6\u3002\u65cb\u84b8\u9664\u53bb\u6325\u53d1\u6027\u7269\u8d28\uff0cresidue\u7528\u4e59\u8148\/\u4e59\u919a\u91cd\u7ed3\u6676\u3002 \u4ea7\u73871.28 g\uff0865\uff05\uff09 \u53c2\u8003\u6587\u732e Englund, E. A.; Gopi, H. 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