(2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate | 51056-25-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
• 英文别名: benzyl 6α-hydroxypenicillanante；benzyl 6α-hydroxypenicillanate；benzyl 6α-hydroxypenicillinate；6α-hydroxy-penicillanic acid benzyl ester；benzyl 6-α-hydroxypenicillanate；benzyl 6-alpha-hydroxypenicillanate；benzyl (2S,5R,6S)-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 51056-25-8
• 化学式: C₁₅H₁₇NO₄S
• 分子量: 307.37
• InChiKey: XZNVUJIUQOYXIH-GMXVVIOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 在 palladium on activated charcoal 叠氮化锂 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.25h， 生成 6-氨基青霉烷酸
  参考文献：
  名称：

  Total syntheses of penicillanic acid S,S-dioxide and 6-aminopenicillanic acid using (benzyloxy)nitromethane

  摘要：

  DOI：

  10.1021/jo00304a024
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 高氯酸 、 三乙胺 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.33h， 生成 (2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
  参考文献：
  名称：

  Synthesis of 6-vinylidenepenams

  摘要：

  The preparation of unique penicillin derivatives containing an exocyclic allene at the 6 position (6-vinylidenepenams) is described. The synthetic scheme utilizes 6-oxopenicillinates as intermediates which stereospecifically add acetylide anions forming propargylic alcohols. Displacement of the corresponding propargylic triflates with higher order cuprate reagents and with copper(I) halides proceeds rapidly and stereospecifically. Halogen-metal exchange of the 6-(halovinylidene)penams is described. The derived allenyl anions can be trapped by electrophiles. Conversion of selected allyl and benzhydryl esters to the corresponding carboxylic acids is described. The beta-lactamase inhibitory activity of the 6-(tert-butylvinylidene)penam sulfone is documented.

  DOI：

  10.1021/jo00058a008

文献信息

• DEACETYLATION OF BENZYL 6α-ACETOXYPENICILLANATE
  作者：SAMIR M. BADR EL-DIN、KENNETH R. HENERY-LOGAN

  DOI：10.7164/antibiotics.26.697

  日期：——

  Benzyl 6α-acetoxypenicillanate was transformed into benzyl 6α-hydroxypenicillanate by enzymatic cleavage of the acetyl group. The preparation of several side chain oxygen analogues of the penicillins is described.

  6α- 乙酰氧基青霉烷酸苄酯通过乙酰基的酶裂解转化为 6α- 羟基青霉烷酸苄酯。文中介绍了几种青霉素侧链氧类似物的制备方法。
• Penicillin derivatives as anti-inflammatory and antidegenerative agents
  申请人：Merck & Co., Inc.

  公开号：EP0170192A1

  公开（公告）日：1986-02-05

  Derivatives of Penicillin, their sulfoxides and sulfones of the structural formula: wherein q is 0, 1 or 2; A is, e.g., CH3 or CH2O(CO)CH3; R, is, e.g., R'NR. wherein R. is H or C1-6alkyl and R' is, e.g., hydrogen or where R represents: (i) hydrogen; (ii) C1-6alkyl; (iii) trifluoromethyl or methoxymethyl; (iv) thienyl; (v) phenyl; or (vi) mono- and disubstituted phenyl and thienyl wherein the substituents are selected from the group consisting of chloro, bromo, fluoro, nitro, loweralkyl, and loweralkoxy; n is 0 or 1; B is, e.g., hydrogen or alkyl and R is, e.g., H or halo; are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.

  青霉素的衍生物、其结构式为硫醚和砜的衍生物： 其中 q 是 0、1 或 2； A 是 CH3 或 CH2O(CO)CH3 等； 其中 R. 是 H 或 C1-6 烷基，R'是氢或 C1-6 烷基。 其中 R 代表 (i) 氢 (ii) C1-6 烷基 (iii) 三氟甲基或甲氧基甲基 (iv) 噻吩基 (v) 苯基；或 (vi) 单取代和二取代苯基和噻吩基，其中取代基选自由氯、溴、氟、硝基、低级烷基和低级烷氧基组成的组； n 为 0 或 1； B 是氢或烷基，以及 R 是氢或卤素； 是有效的弹性蛋白酶抑制剂，因此是有用的抗炎/抗变性制剂。
• 6-(Substituted) methylenepenicillanic and 6-(substituted) hydroxymethylpenicillanic acids and derivatives thereof
  申请人：PFIZER INC.

  公开号：EP0150984B1

  公开（公告）日：1991-09-11
• Synthesis and human leukocyte elastase inhibitory evaluation of phosphate triesters and acyl phosphates of penam sulfides and sulfones
  作者：Marı́a Laborde、Germán Pezzenati、Patricia Yovaldi、Oreste A. Mascaretti、Rolando C. Rossi、Juan Pablo Rossi

  DOI：10.1016/s0968-0896(01)00139-0

  日期：2001.8

  The synthesis of 6,6-dibromo-3 alpha-(diphenylphosphate)oxymethyl-2,2-dimethyl penam sulfone (3a), 6 alpha -chloro-3 alpha-(diphenylphosphate)oxymethyl-2,2-dimethyl penam sulfone (3b), benzyl 6 alpha-(diphenyl-phosphate)oxypenicillanate sulfone (4) and 6,6-dibromo-3 alpha-(methylphosphate)carbonyl-2,2-dimethylpenam sulfone (12) are reported. When tested as inhibitors of human leukocyte elastase, the compound 4 proved to be the most active. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of 6-hydroxypenicillanates and 7-hydroxycephalosporanates
  作者：John C. Sheehan、Young S. Lo、Jurg Loliger、Clifford C. Podewell

  DOI：10.1021/jo00926a034

  日期：1974.5