(2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate | 52141-84-1

• 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: (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
• 英文别名: diphenylmethyl 6β-(2-phenoxyacetamido)penicillanate；benzhydryl (3S,5R,6R)-6-phenoxyacetylaminopenicillanate；Diphenylmethyl 6beta-phenoxyacetamido-2,2-dimethylpenam-3alpha-carboxylate；benzhydryl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 52141-84-1
• 化学式: C₂₉H₂₈N₂O₅S
• 分子量: 516.618
• InChiKey: NIRLNJOAFBCHAG-NRRYGQPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 在 双氧水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以91%的产率得到二苯基甲基 [2S-(2alpha,5alpha,6beta)]-3,3-二甲基-7-氧代-6-(苯氧基乙酰氨基)-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸酯 4-氧化物
  参考文献：
  名称：

  Micetich, Ronald G.; Singh, Rajeshwar; Maiti, Samarendra N., Heterocycles, 1984, vol. 22, # 3, p. 531 - 535

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯甲醇 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  Convenient Formation of Diphenylmethyl Esters Using Diphenylmethyl Trichloroacetimidate

  摘要：

  Diphenylmethyl trichloroacetimidate is a useful reagent for the protection of carboxylic acids as their corresponding diphenylmethyl esters. These esterifications proceed rapidly without the need for an added catalyst or promoter. A variety of carboxylic acid substrates undergo esterification in excellent yields with the trichloroacetimidate reagent, including substrates possessing acid- or base-sensitive functionality. Protection of a carboxylic acid with a highly enolizable alpha-stereocenter using diphenylmethyl imidate was also accomplished without racemization.

  DOI：

  10.1055/s-0033-1340293

文献信息

• Process for the preparation of esters of N-blocked penicillin acids
  申请人：Glaxo Laboratories Limited

  公开号：US03960843A1

  公开（公告）日：1976-06-01

  A process is described for the preparation of esters of N-blocked amino acids (such as penicillins or cephalosporins) wherein the amino acid or a salt thereof is reacted with a primary amine and nitrosating agent.

  本文描述了一种制备N-保护氨基酸酯（如青霉素或头孢菌素）的过程，其中氨基酸或其盐与一种主要胺和亚硝酰化剂反应。
• 2,4,6-Tripyridino-1,3,5-triazine Trichloride, a New and Mild Esterification Agent for Preparation of Penicillin Esters
  作者：Masayuki Murakami、Makoto Hajima、Fumitaka Takami、Mitsuru Yoshioka

  DOI：10.3987/com-90-5565

  日期：——

  Cyanuric chloride reacted with 3 molar equivalents of pyridine to give 2,4,6-tripyridinio-1,3,5-triazine trichloride, which was found to condense penicillins with alcohols under mild conditions to afford penicillin esters in good yields. Application to preparation of cephalosporin esters also is discussed.
• Spry, Douglas O.; Snyder, Nancy J.; Bhala, Anita R., Heterocycles, 1987, vol. 26, # 11, p. 2911 - 2920
  作者：Spry, Douglas O.、Snyder, Nancy J.、Bhala, Anita R.、Pasini, Carol E.、Indelicato, Joseph M.

  DOI：——

  日期：——
• Sammes, Peter G.; Smith, Steven; Woolley, Geoffrey T., Journal of the Chemical Society. Perkin transactions I, 1984, # 11, p. 2603 - 2610
  作者：Sammes, Peter G.、Smith, Steven、Woolley, Geoffrey T.

  DOI：——

  日期：——
• Baldwin, Jack E.; Adlington, Robert M.; Kang, Tae Won, Heterocycles, 1989, vol. 28, # 2, p. 759 - 766
  作者：Baldwin, Jack E.、Adlington, Robert M.、Kang, Tae Won、King, Lionel G.、Patel, Vipulkumar K.

  DOI：——

  日期：——