(S)-2-((E)-4-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-3-oxo-but-1-enyl)-pyrrolidine-1-carboxylic acid allyl ester | 126407-73-6

• 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: (S)-2-((E)-4-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-3-oxo-but-1-enyl)-pyrrolidine-1-carboxylic acid allyl ester
• 英文别名: (3S,4R)-4-[(E)-4-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine；prop-2-enyl (2S)-2-[(E)-4-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-2-methyl-3-oxobut-1-enyl]pyrrolidine-1-carboxylate
• CAS: 126407-73-6
• 化学式: C₂₄H₄₀N₂O₅Si
• 分子量: 464.678
• InChiKey: OUWLCOJVJZMFPP-DWRJUMKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-((E)-4-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-3-oxo-but-1-enyl)-pyrrolidine-1-carboxylic acid allyl ester 在 四(三苯基膦)钯 四丁基氟化铵 、 5,5-二甲基-1,3-环己二酮 、 溶剂黄146 作用下， 生成 (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(E)-2-{(2S)-pyrrolidin-2-yl]-1-methylethenyl]-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-vinyl carbapenems. Remarkable DHP-1 stability of 1′-substituted analogs

  摘要：

  The synthesis, antibacterial activity and DHP-susceptibility of a series of novel 2-vinyl carbapenems is described. Carbapenems having a 1'-substituted vinyl moiety at the 2 position were found to be very stable toward DHP-1, displaying comparable stability to compounds with a 1 beta-methyl functionality. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00495-7
• 作为产物：
  描述：

  (2S)-1-allyloxycarbonyl-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine 在 三乙胺 、 zinc dibromide 作用下， 生成 (S)-2-((E)-4-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-methyl-3-oxo-but-1-enyl)-pyrrolidine-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-vinyl carbapenems. Remarkable DHP-1 stability of 1′-substituted analogs

  摘要：

  The synthesis, antibacterial activity and DHP-susceptibility of a series of novel 2-vinyl carbapenems is described. Carbapenems having a 1'-substituted vinyl moiety at the 2 position were found to be very stable toward DHP-1, displaying comparable stability to compounds with a 1 beta-methyl functionality. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00495-7

文献信息

• 3-Alkenyl-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid compounds
  申请人：Fujisawa Pharmaceutical Company, Ltd.

  公开号：US04923857A1

  公开（公告）日：1990-05-08

  The invention relates to an antimicrobial compound of the formula: ##STR1## in which R.sup.1 is carboxy or protected carboxy, R.sup.2 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl, R.sup.3 and R.sup.4 are each hydrogen or lower alkyl, and R.sup.5 is saturated 4 to 6-membered heteromonocyclic group containing 1 to 4 nitrogen atom(s), saturated 5 or 6-membered heteromonocyclic group containing 1 to 2 oxygen atom(s) and 1 to 3 nitrogen atom(s) or saturated 5 or 6-membered heteromonocyclic group containing 1 to 2 sulfur atom(s) and 1 to 3 nitrogen atom(s), wherein said aliphatic heterocyclic group may be substituted by one or more suitable substituent(s) selected from a group consisting of hydroxy, protected hydroxy, hydroxy(lower)alkyl, protected hydroxy(lower)alkyl, halogen, lower alkoxy, lower alkyl, lower alkoxy(lower)alkyl, imino, protected imino, lower alkylamino, protected lower alkylamino, mono(or di)-(lower)alkylcarbamoyloxy, lower alkylidene, lower alkanimidoyl and imino-protective group, or pharmaceutically acceptable salts thereof.

  本发明涉及一种抗微生物化合物，其化学式为：##STR1## 其中，R.sup.1是羧基或保护羧基，R.sup.2是羟基（较低）烷基或保护羟基（较低）烷基，R.sup.3和R.sup.4分别是氢或较低烷基，R.sup.5是饱和的4至6元杂环基，包含1至4个氮原子，饱和的5或6元杂环基，包含1至2个氧原子和1至3个氮原子，或饱和的5或6元杂环基，包含1至2个硫原子和1至3个氮原子，其中所述的脂环杂环基可以被一个或多个适当的取代基所取代，所述取代基被选自羟基，保护羟基，羟基（较低）烷基，保护羟基（较低）烷基，卤素，较低烷氧基，较低烷基，较低烷氧基（较低）烷基，亚氨基，保护亚氨基，较低烷基氨基，保护较低烷基氨基，单（或双）-（较低）烷基氨基甲酰氧基，较低烷基亚甲基，较低烷基亚胺基和亚胺保护基所选的适当取代基组成，或其药学上可接受的盐。
• 3-alkenyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds
  申请人：Fujisawa Pharmaceutical Company, Ltd.

  公开号：US05081237A1

  公开（公告）日：1992-01-14

  The invention relates to novel intermediate compounds for preparation of compounds of high antimicrobial activity, said intermediate compounds being of one of the formulas: ##STR1## wherein R.sup.1 is carboxy or protected carboxy, R.sup.2 is hydroxy(lower)alkyl or protected hyroxy(lower)alkyl, R.sup.3 and R.sup.4 are each hydrogen or lower alkyl, R.sup.5 is a saturated heterocyclic group, and R.sup.6 is aryl or lower alkoxy, or pharmaceutically acceptable salts thereof.

  本发明涉及用于制备高抗微生物活性化合物的新型中间体化合物，所述中间体化合物为以下公式之一：##STR1## 其中R.sup.1是羧基或保护羧基，R.sup.2是羟基（较低）烷基或保护羟基（较低）烷基，R.sup.3和R.sup.4分别是氢或较低烷基，R.sup.5是饱和杂环基，R.sup.6是芳基或较低烷氧基，或其药学上可接受的盐。