(3SR,4RS)-3-[1(SR)-hydroxyethyl]-2-oxoazetidine-4-yl-acetic acid benzyl ester | 77120-96-8

• 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: (3SR,4RS)-3-[1(SR)-hydroxyethyl]-2-oxoazetidine-4-yl-acetic acid benzyl ester
• 英文别名: benzyl 2-[3-(1-hydroxyethyl)-4-oxoazetidin-2-yl]acetate
• CAS: 77120-96-8；78477-86-8；78919-18-3；84985-44-4；89615-92-9
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: VEOGAZMGGUEDBF-UHFFFAOYSA-N

物化性质

• 沸点：
  473.1±15.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3SR,4RS)-3-[1(SR)-hydroxyethyl]-2-oxoazetidine-4-yl-acetic acid benzyl ester 生成 (3RS,4RS)-3-[1(RS)-fluoroethyl]-2-oxoazetidine-4-yl-acetic acid benzylester
  参考文献：
  名称：

  MAK, CHING P.;FLIRI, HANS

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Amino-2-(1-hydroxyethyl)-5-oxo-5-phenylmethoxypentanoic acid 生成 (3SR,4RS)-3-[1(SR)-hydroxyethyl]-2-oxoazetidine-4-yl-acetic acid benzyl ester
  参考文献：
  名称：

  MELILLO, D. G.;RYAN, K. M.

  摘要：

  DOI：

文献信息

• Further studies on the acetonedicarboxylate route to thienamycin—stereochemical inversion at the lactone stage.
  作者：D.G. Melillo、T. Liu、K. Ryan、M. Sletzinger、I. Shinkal

  DOI：10.1016/0040-4039(81)89007-7

  日期：1981.1

  Stereochemical inversion of an easily prepared δ-lactone has culiminated in the preparation of a key intermediate for the synthesis of thienamycin.

  易于制备的δ-内酯的立体化学转化在制备噻吩霉素的关键中间体的制备中已被取消。
• Fluoralkylatedcarbapenem derivatives
  申请人：Sandoz Ltd.

  公开号：US04720490A1

  公开（公告）日：1988-01-19

  6-(1'-fluorethyl)- and 6-(1'-fluoro-1'-methylethyl)-carbapenems such as (5RS,6RS)-1-aza-6-(1(RS)-fluorethyl)-3-(N'-dimethyl-N'-methylamidinomethyl thio)-7-oxobicyclo[3.2.0]hept-2-ene-2-carboxylic acid which are useful as chemotherapeutic agents in particular as anti-bacterially active anti-biotics.

  6-(1'-氟乙基)-和6-(1'-氟-1'-甲基乙基)-头孢菌素，例如(5RS,6RS)-1-氮杂-6-(1(RS)-氟乙基)-3-(N'-二甲基-N'-甲基氨基甲硫基)-7-氧代双环[3.2.0]庚-2-烯-2-羧酸，这些化合物在特定情况下可用作化疗药物，特别是作为抗菌活性抗生素。
• Efficient Method for the Deprotection of <i>tert</i>-Butyldimethylsilyl Ethers with TiCl₄−Lewis Base Complexes:  Application to the Synthesis of 1β-Methylcarbapenems
  作者：Akira Iida、Hiroki Okazaki、Tomonori Misaki、Makoto Sunagawa、Akira Sasaki、Yoo Tanabe

  DOI：10.1021/jo0604484

  日期：2006.7.1

  TiCl4-Lewis base (AcOEt, CH3NO2) complexes smoothly deprotected tert-butyldimethylsilyl (TBDMS) ethers. The reaction velocity with these complexes, which seemed less reactive due to the influence of Lewis bases, was considerably greater than that with TiCl4 alone. Selective desilylations between aliphatic and aromatic TBDMS ethers (1 and 5), between 1 and benzyl, allyl, tosyl, methoxyphenyl, and chloroacetyl ethers (13, 14, 15, 16, and 17), and between TBDMS and TBDPS ethers (18 and 19) were successfully performed. Desilylation of TBDMS-aldol, acyloin, and beta-lactam analogues 9-12 proceeded smoothly due to anchimeric assistance by the neighboring carbonyl groups. The present method was successfully applied to the practical synthesis of 1 beta-methylcarbapenems 20a'-f'.
• MAK, CHING P.;FLIRI, HANS
  作者：MAK, CHING P.、FLIRI, HANS

  DOI：——

  日期：——
• MELILLO, D. G.;RYAN, K. M.
  作者：MELILLO, D. G.、RYAN, K. M.

  DOI：——

  日期：——