6β-phthalimido-penicillanic acid benzhydryl ester | 34716-54-6

• 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: 6β-phthalimido-penicillanic acid benzhydryl ester
• 英文别名: benzhydryl (2S,5R,6R)-6-(1,3-dioxoisoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 34716-54-6
• 化学式: C₂₉H₂₄N₂O₅S
• 分子量: 512.586
• InChiKey: QRDFDMYDTGRIGC-MRCUYLHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6β-phthalimido-penicillanic acid benzhydryl ester 在 氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 diphenylmethyl (2S)-2-[(3R,4S)-4-chloro-3-phthalimido-2-oxazetidin-1-yl]-2-(1-chlorothio-1-methylethyl)-acetate
  参考文献：
  名称：

  Syntheses of (6S)-Cephalosporins from 6-Aminopenicillanic Acid

  摘要：

  Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the second, ester 15 was converted to (2S,4S,5S,6R)-penicillin sulfoxide 58, which was then transformed into (6S,7R)-cephem 59. Different methods for the epimerisation of the C-7 position of cephem 59 were examined. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00486-5
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.08h， 生成 6β-phthalimido-penicillanic acid benzhydryl ester
  参考文献：
  名称：

  Syntheses of (6S)-Cephalosporins from 6-Aminopenicillanic Acid

  摘要：

  Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the second, ester 15 was converted to (2S,4S,5S,6R)-penicillin sulfoxide 58, which was then transformed into (6S,7R)-cephem 59. Different methods for the epimerisation of the C-7 position of cephem 59 were examined. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00486-5

文献信息

• Direct introduction of a benzoyloxy substituent at the ring junction of fused β-lactam rings
  作者：Hiromu Matsumura、Toshisada Yano、Masako Ueyama、Kazuo Tori、Wataru Nagata

  DOI：10.1039/c39790000485

  日期：——

  7-phthalimido-3-methyl-ceph-3-em-4-carboxylate (1) and 6-phthalimido-penicillins (4) with t-butyl perbenzoate in the presence of copper(I) chlride gave compounds bearing a benzoyloxy substitutent at the ring junction of the fused β-lactam rings, (2) and (5) respectively.

  在过氧化铜（I）存在下用过苯甲酸叔丁酯处理7-邻苯二甲酰亚胺-3-甲基ceph-3-em-4-羧酸盐（1）和6-邻苯二甲酰亚胺-青霉素（4）。在稠合的β-内酰胺环的环连接处分别为（2）和（5）的苯甲酰氧基取代基。
• Novel stereochemical manipulations of the penicillin nucleus
  作者：Jack E. Baldwin、Robert Y. Chan、John D. Sutherland

  DOI：10.1016/s0040-4039(00)73540-4

  日期：1994.7

  The synthesis of a homochiral C2-epipenicillin tert-butyl amide 1 from 6-β-phthalimidopenicillanic acid is described.

  描述了由6-β-邻苯二甲酰亚胺基Openicillanic酸合成高手性的C2-哌啶青霉素叔丁基酰胺1。
• Lattrell, Justus Liebigs Annalen der Chemie, 1974, vol. No. 12, p. 1937 - 1954
  作者：Lattrell

  DOI：——

  日期：——
• US3962276A
  申请人：——

  公开号：US3962276A

  公开（公告）日：1976-06-08
• Syntheses of (6S)-Cephalosporins from 6-Aminopenicillanic Acid
  作者：Tomasz Fekner、Jack E Baldwin、Robert M Adlington、Timothy W Jones、C.Keith Prout、Christopher J Schofield

  DOI：10.1016/s0040-4020(00)00486-5

  日期：2000.8

  Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the second, ester 15 was converted to (2S,4S,5S,6R)-penicillin sulfoxide 58, which was then transformed into (6S,7R)-cephem 59. Different methods for the epimerisation of the C-7 position of cephem 59 were examined. (C) 2000 Elsevier Science Ltd. All rights reserved.