(4S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxymethyl-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 104618-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxymethyl-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (4S,5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-(hydroxymethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 104618-38-4
• 化学式: C₂₀H₃₃NO₅Si
• 分子量: 395.571
• InChiKey: LCCMZUXNVAQTAC-SJXGUFTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxymethyl-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到prop-2-enyl (4S,5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-formyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of 2α-functionalized 1β-methylcarbapenems related to KR-21012

  摘要：

  The 2 alpha-functionalized 1 beta-merhylcarbapenems 3 were synthesized from the 2-formyl 1 beta-methylcarbapenem intermediate 5. The best compound in the series of 2 alpha-(hydroxy)alkylcarbapenems, KR-21012, displayed well balanced in vitro and in vivo activity as a parent compound of oral carbapenem. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00692-7
• 作为产物：
  描述：

  (3S,4S)-3-[(R)-1-(叔丁基二甲基硅氧基)乙基]-4-[(R)-1-羰乙基]-2-氮杂环丁酮 在 2,6-二甲基吡啶 、 磺酰氯 、 甲基溴化镁 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 39.0h， 生成 (4S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxymethyl-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis of 2-(Hydroxymethyl)-1β-methylcarbapenem. Chemoselective Organometallic Addition to 3-Substituted 4-[(R)-1-Carboxyethyl]azetidin-2-one

  摘要：

  DOI：

  10.1021/jo9716845

文献信息

• New applications of the mitsunobu reaction in the synthesis of C-2 N-methyl carbapenems
  作者：J.C. Arnould、F. Landier、M.J. Pasquet

  DOI：10.1016/s0040-4039(00)60855-9

  日期：1992.11

  N-acyl amides and N-acylamino heterocycles can be reacted regioselectively with C-2 hydroxymethyl carbapenems under Mitsunobu conditions:synthesis of amides, exocyclic alkylation of amino heterocycles and transformation into 2-aminomethyl carbapenems are reported.

  N-酰基酰胺和N-酰基氨基杂环可以在Mitsunobu条件下与C-2羟甲基碳青霉烯发生区域选择性反应：酰胺的合成，氨基杂环的环外烷基化和转化为2-氨基甲基碳青霉烯的报道。
• Synthesis and antibacterial activity of 2α-functionalized 1β-methylcarbapenems related to KR-21012
  作者：Hyun J. Kwak、Do K. Pyun、Jae H. Kim、Eun J. Kim、Hee J. Jeong、Bong J. Kim、Cheol H. Lee

  DOI：10.1016/s0960-894x(99)00692-7

  日期：2000.2

  The 2 alpha-functionalized 1 beta-merhylcarbapenems 3 were synthesized from the 2-formyl 1 beta-methylcarbapenem intermediate 5. The best compound in the series of 2 alpha-(hydroxy)alkylcarbapenems, KR-21012, displayed well balanced in vitro and in vivo activity as a parent compound of oral carbapenem. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of 2-(Hydroxymethyl)-1β-methylcarbapenem. Chemoselective Organometallic Addition to 3-Substituted 4-[(<i>R</i>)-1-Carboxyethyl]azetidin-2-one
  作者：X. Eric Hu、Thomas P. Demuth

  DOI：10.1021/jo9716845

  日期：1998.3.1