{"id":179,"date":"2014-01-10T11:34:54","date_gmt":"2014-01-10T03:34:54","guid":{"rendered":"\/\/www.gsbet888.com\/?p=179"},"modified":"2019-08-02T18:57:21","modified_gmt":"2019-08-02T10:57:21","slug":"%e5%af%b9%e7%94%b2%e6%b0%a7%e5%9f%ba%e8%8b%84%e5%9f%ba%e4%bf%9d%e6%8a%a4%e5%9f%bap-methoxybenzyl-pmb-protective-group","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2014\/01\/%e5%af%b9%e7%94%b2%e6%b0%a7%e5%9f%ba%e8%8b%84%e5%9f%ba%e4%bf%9d%e6%8a%a4%e5%9f%bap-methoxybenzyl-pmb-protective-group.html","title":{"rendered":"\u5bf9\u7532\u6c27\u57fa\u82c4\u57fa\u4fdd\u62a4\u57fap-Methoxybenzyl (PMB) Protective Group"},"content":{"rendered":"<p align=\"left\">\u9187\u2192\u4e59\u919a<\/p>\n<ul>\n<li><strong>\u6982\u8981<\/strong><\/li>\n<\/ul>\n<p align=\"left\"><i>p<\/i>-\u7532\u6c27\u57fa\u82c4\u57fa\uff08PMB or MPM\uff09\u548c\u82c4\u57fa\u4e00\u6837\u80fd\u5bf9\u7f9f\u57fa\u8fdb\u884c\u4fdd\u62a4\u30fb\u8131\u4fdd\u62a4\u3002\u53ef\u4ee5\u5229\u7528DDQ(\u4e8c\u6c2f\u4e8c\u6c30\u5bf9\u82ef\u918c)\u5728\u6e29\u548c\u6c27\u5316\u6761\u4ef6\u4e0b\uff0c\u6216\u5728\u5f3a\u9178\u6027\u6761\u4ef6\u4e0b\u4f7f\u5176\u8131\u53bb\u3002<\/p>\n<p align=\"left\">\u4e8c\u7532\u6c27\u57fa\u82c4\u57fa\u6709\u4e24\u79cd\uff0c\u7532\u6c27\u57fa\u5206\u522b\u57282,4\u4f4d\uff08DMB\uff09\u62163,4\u4f4d\uff08DMPM\uff09\u3002\uff08DMB or DMPM\uff09\u6bd4PMB\u80fd\u5728\u66f4\u6e29\u548c\u7684\u6761\u4ef6\u4e0b\u8fdb\u884c\u8131\u4fdd\u62a4\u3002<\/p>\n<p>PMB\u4e09\u6c2f\u4e59\u9170\u4e9a\u80fa(PMB-O\uff08C=NH\uff09CCl<sub>3<\/sub>)\u53ef\u4ee5\u4f7fPMB\u5728\u9178\u6027\u6761\u4ef6\u4e0b\u4fdd\u62a4\u3002\u5bf9\u78b1\u4e0d\u7a33\u5b9a\u7684\u5316\u5408\u7269\u4e5f\u9002\u7528\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u57fa\u672c\u6587\u732e<\/strong><\/li>\n<\/ul>\n<p>\u30fbMarco, J. L.; Hueso-Rodriguez, J. A.\u00a0<em>Tetrahedron Lett.<\/em>\u00a0<strong>1988<\/strong>,\u00a0<em>29<\/em>, 2459.<br \/>\n\u30fbHorita, K.; Abe, R.; Yonemitsu, O.\u00a0<em>Tetrahedron Lett.<\/em>\u00a0<strong>1988<\/strong>,\u00a0<em>29<\/em>, 4139.<br \/>\n\u30fbHorita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y. Yonemitsu, O.\u00a0<em>Tetrahedron<\/em>\u00a0<strong>1986<\/strong>,\u00a0<em>42<\/em>, 3021.<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u673a\u7406<\/strong><\/li>\n<\/ul>\n<p>1.\u4fdd\u62a4<\/p>\n<p>\u672c\u53cd\u5e94\u673a\u7406\u548cWilliamson\u5408\u6210\u53cd\u5e94\u76f8\u540c<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb.ht2_.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"pmb.ht2\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb.ht2_.gif\" width=\"390\" height=\"82\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p align=\"left\">2.\u8131\u4fdd\u62a4(DDQ)<\/p>\n<p>\u5f62\u6210\u7684\u7535\u8377\u8f6c\u79fb\u914d\u5408\u7269\u4f7f\u53cd\u5e94\u7269\u6c27\u5316\u3001\u7136\u540e\u901a\u8fc7\u6c34\u89e3\u5b8c\u6210\u8131\u4fdd\u62a4\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb.ht3_.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"pmb.ht3\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb.ht3_.gif\" width=\"423\" height=\"184\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/li>\n<\/ul>\n<p align=\"left\">DIBAL\u8fd8\u539f\u4e9a\u82c4\u57fa\u7f29\u919b(\u6216\u7532\u6c27\u57fa\u82c4\u57fa\u7f29\u919b)\u65f6\uff0c\u4e0e\u7f29\u919b\u4e0a\u7acb\u4f53\u4f4d\u963b\u5c0f\u7684\u6c27\u539f\u5b50\u4f5c\u7528\u540e\uff0c\u4f7f\u5355\u4fa7\u78b3\u6c27\u952e\u65ad\u88c2\u5f00\u73af\u3002<\/p>\n<p align=\"left\"><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb_8.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"pmb_8\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb_8.gif\" width=\"391\" height=\"194\" \/><\/a><\/p>\n<p align=\"left\">PMB\uff08Bn\uff09\u57fa\u7684\u8fc1\u79fb\uff1a\u5229\u7528DIBAL\u5f15\u8d77\u7684\u4e9a\u82c4\u57fa\u7f29\u919b\u7684\u5f00\u73af\u53cd\u5e94\uff0c\u80fd\u4f7fPMB\uff08Bn\uff09\u57fa\u8f6c\u79fb\u5230\u4f4d\u963b\u5927\u7684\u7f9f\u57fa\u4e0a\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb_7.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"pmb_7\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb_7.gif\" width=\"403\" height=\"126\" \/><\/a><\/p>\n<p>\u82ef\u8fde\u63a5\u7684\u7532\u6c27\u57fa\u8d8a\u591a\uff0c\u8131\u4fdd\u62a4\u8d8a\u7b80\u5355\u3002\u5728PMB\u7684\u5b58\u5728\u4e0b\uff0c\u53ef\u4ee5\u6709\u9009\u62e9\u7684\u8131\u53bbDMB \u3002[1]\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb_6.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"pmb_6\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb_6.gif\" width=\"297\" height=\"123\" \/><\/a><\/p>\n<p>(+)-Saxtoxin\u7684\u5408\u6210[2]\uff1a\u5229\u7528PMB\u7684\u7ed9\u96fb\u5b50\u6027\uff0c\u80fd\u51cf\u7f13\u78fa\u9170\u80fa\u7684\u5438\u7535\u5b50\u6027\u3001\u800c\u7a33\u5b9a\u4e0b\u5217\u7684\u53cd\u5e94\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb_5.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"pmb_5\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb_5.gif\" width=\"363\" height=\"233\" \/><\/a><\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6b65\u9aa4<\/strong><\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6280\u5de7<\/strong><\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53c2\u8003\u6587\u732e<\/strong><\/li>\n<\/ul>\n[1]\u00a0<em>Tetrahedron<\/em>\u00a0<strong>1986<\/strong>,\u00a0<em>42<\/em>, 3021.<br \/>\n[2] (a) Fleming, J. J.; Du Bois, J.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong>2006<\/strong>,\u00a0<em>128<\/em>, 3926.DOI:\u00a0<a href=\"http:\/\/dx.doi.org\/10.1021\/ja0608545\">10.1021\/ja0608545<\/a>\u00a0(b) Fleming, J. J.; McReynolds, M. D.; Du Bois, J.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong>2007<\/strong>,\u00a0<em>129<\/em>, 9964. DOI:<a href=\"http:\/\/dx.doi.org\/10.1021\/ja071501o\">10.1021\/ja071501o<\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u76f8\u5173\u4e66\u7c4d<\/strong><\/li>\n<\/ul>\n[amazonjs asin=&#8221;0471697540&#8243; locale=&#8221;CN&#8221; title=&#8221;Greene&#8217;s Protective Groups in Organic Synthesis&#8221;][amazonjs asin=&#8221;1588903761&#8243; locale=&#8221;CN&#8221; title=&#8221;Protecting Groups&#8221;]\n<ul>\n<li><strong>\u76f8\u5173\u94fe\u63a5<\/strong><\/li>\n<\/ul>\n<p>\u30fb<a href=\"http:\/\/ja.wikipedia.org\/wiki\/%E4%BF%9D%E8%AD%B7%E5%9F%BA\">\u4fdd\u8b77\u57fa<\/a>\u00a0(Wikipedia\u65e5\u672c)<br \/>\n\u30fb<a href=\"http:\/\/en.wikipedia.org\/wiki\/Protecting_group\">Protecting Group<\/a>(Wikipedia\uff09<br \/>\n\u30fb<a href=\"http:\/\/www.chem.ucalgary.ca\/courses\/351\/Carey5th\/Ch17\/ch17-3-4-3.html\">Protecting Group<\/a><br \/>\n\u30fb<a href=\"http:\/\/www.organic-chemistry.org\/frames.htm?http:\/\/www.organic-chemistry.org\/protectivegroups\/\">Stability of Protecting Group: Hydroxyl<\/a>\u00a0(organic-chemistry.org)<br \/>\n\u30fb<a href=\"http:\/\/www.chem.harvard.edu\/groups\/myers\/handouts\/protectivegroups.pdf\">Protective Groups<\/a>\u00a0(A.Myers&#8217; Group\uff1aPDF) <\/p>\n","protected":false},"excerpt":{"rendered":"\u9187\u2192\u4e59\u919a \u6982\u8981 p-\u7532\u6c27\u57fa\u82c4\u57fa\uff08PMB or MPM\uff09\u548c\u82c4\u57fa\u4e00\u6837\u80fd\u5bf9\u7f9f\u57fa\u8fdb\u884c\u4fdd\u62a4\u30fb\u8131\u4fdd\u62a4\u3002\u53ef\u4ee5\u5229\u7528DDQ(\u4e8c\u6c2f\u4e8c\u6c30\u5bf9\u82ef\u918c)\u5728\u6e29\u548c\u6c27\u5316\u6761\u4ef6\u4e0b\uff0c\u6216\u5728\u5f3a\u9178\u6027\u6761\u4ef6\u4e0b\u4f7f\u5176\u8131\u53bb\u3002 \u4e8c\u7532\u6c27\u57fa\u82c4\u57fa\u6709\u4e24\u79cd\uff0c\u7532\u6c27\u57fa\u5206\u522b\u57282,4\u4f4d\uff08DMB\uff09\u62163,4\u4f4d\uff08DMPM\uff09\u3002\uff08DMB or DMPM\uff09\u6bd4PMB\u80fd\u5728\u66f4\u6e29\u548c\u7684\u6761\u4ef6\u4e0b\u8fdb\u884c\u8131\u4fdd\u62a4\u3002 PMB\u4e09\u6c2f\u4e59\u9170\u4e9a\u80fa(PMB-O\uff08C=NH\uff09CCl3)\u53ef\u4ee5\u4f7fPMB\u5728\u9178\u6027\u6761\u4ef6\u4e0b\u4fdd\u62a4\u3002\u5bf9\u78b1\u4e0d\u7a33\u5b9a\u7684\u5316\u5408\u7269\u4e5f\u9002\u7528\u3002 &nbsp; \u57fa\u672c\u6587\u732e \u30fbMarco, J. L.; Hueso-Rodriguez, J. A.\u00a0Tetrahedron Lett.\u00a01988,\u00a029, 2459. \u30fbHorita, K.; Abe, R.; Yonemitsu, O.\u00a0Tetrahedron Lett.\u00a01988,\u00a029, 4139. \u30fbHorita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y. Yonemitsu, O.\u00a0Tetrahedron\u00a01986,\u00a042, 3021. &nbsp; \u53cd\u5e94\u673a\u7406 1.\u4fdd\u62a4 \u672c\u53cd\u5e94\u673a\u7406\u548cWilliamson\u5408\u6210\u53cd\u5e94\u76f8\u540c &nbsp; 2.\u8131\u4fdd\u62a4(DDQ) \u5f62\u6210\u7684\u7535\u8377\u8f6c\u79fb\u914d\u5408\u7269\u4f7f\u53cd\u5e94\u7269\u6c27\u5316\u3001\u7136\u540e\u901a\u8fc7\u6c34\u89e3\u5b8c\u6210\u8131\u4fdd\u62a4\u3002 &nbsp; \u53cd\u5e94\u5b9e\u4f8b DIBAL\u8fd8\u539f\u4e9a\u82c4\u57fa\u7f29\u919b(\u6216\u7532\u6c27\u57fa\u82c4\u57fa\u7f29\u919b)\u65f6\uff0c\u4e0e\u7f29\u919b\u4e0a\u7acb\u4f53\u4f4d\u963b\u5c0f\u7684\u6c27\u539f\u5b50\u4f5c\u7528\u540e\uff0c\u4f7f\u5355\u4fa7\u78b3\u6c27\u952e\u65ad\u88c2\u5f00\u73af\u3002 PMB\uff08Bn\uff09\u57fa\u7684\u8fc1\u79fb\uff1a\u5229\u7528DIBAL\u5f15\u8d77\u7684\u4e9a\u82c4\u57fa\u7f29\u919b\u7684\u5f00\u73af\u53cd\u5e94\uff0c\u80fd\u4f7fPMB\uff08Bn\uff09\u57fa\u8f6c\u79fb\u5230\u4f4d\u963b\u5927\u7684\u7f9f\u57fa\u4e0a\u3002 \u82ef\u8fde\u63a5\u7684\u7532\u6c27\u57fa\u8d8a\u591a\uff0c\u8131\u4fdd\u62a4\u8d8a\u7b80\u5355\u3002\u5728PMB\u7684\u5b58\u5728\u4e0b\uff0c\u53ef\u4ee5\u6709\u9009\u62e9\u7684\u8131\u53bbDMB \u3002[1] (+)-Saxtoxin\u7684\u5408\u6210[2]\uff1a\u5229\u7528PMB\u7684\u7ed9\u96fb\u5b50\u6027\uff0c\u80fd\u51cf\u7f13\u78fa\u9170\u80fa\u7684\u5438\u7535\u5b50\u6027\u3001\u800c\u7a33\u5b9a\u4e0b\u5217\u7684\u53cd\u5e94\u3002 \u5b9e\u9a8c\u6b65\u9aa4 &nbsp; \u5b9e\u9a8c\u6280\u5de7 &nbsp; \u53c2\u8003\u6587\u732e [1]\u00a0Tetrahedron\u00a01986,\u00a042, 3021. [2] (a) Fleming, J. J.; Du Bois, J.\u00a0J. Am. Chem. Soc.\u00a02006,\u00a0128, 3926.DOI:\u00a010.1021\/ja0608545\u00a0(b) Fleming, J. J.; McReynolds, M. D.; Du Bois, J.\u00a0J. Am. Chem. Soc.\u00a02007,\u00a0129, 9964. DOI:10.1021\/ja071501o &nbsp; \u76f8\u5173\u4e66\u7c4d [amazonjs asin=&#8221;0471697540&#8243; locale=&#8221;CN&#8221; title=&#8221;Greene&#8217;s Protective Groups in Organic Synthesis&#8221;][amazonjs asin=&#8221;1588903761&#8243; locale=&#8221;CN&#8221; title=&#8221;Protecting Groups&#8221;] \u76f8\u5173\u94fe\u63a5 \u30fb\u4fdd\u8b77\u57fa\u00a0(Wikipedia\u65e5\u672c) \u30fbProtecting Group(Wikipedia\uff09 \u30fbProtecting Group \u30fbStability of Protecting Group: [&hellip;]","protected":false},"author":8,"featured_media":182,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","enabled":false},"version":2}},"categories":[4,2],"tags":[75,76,62,41],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/pmb.ht1_.gif","jetpack_shortlink":"https:\/\/wp.me\/p96op1-2T","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/179"}],"collection":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/users\/8"}],"replies":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/comments?post=179"}],"version-history":[{"count":2,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/179\/revisions"}],"predecessor-version":[{"id":28306,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/179\/revisions\/28306"}],"wp:featuredmedia":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media\/182"}],"wp:attachment":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media?parent=179"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/categories?post=179"},{"taxonomy":"post_tag","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/tags?post=179"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}