(6R,7R)-4-methoxybenzyl 3-(acetoxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 107447-98-3

• 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: (6R,7R)-4-methoxybenzyl 3-(acetoxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 英文别名: (4-methoxyphenyl)methyl (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 107447-98-3
• 化学式: C₂₆H₂₆N₂O₇S
• 分子量: 510.568
• InChiKey: SUYZOYHGJQQBDX-RCZVLFRGSA-N

物化性质

• 熔点：
  112-115 °C
• 沸点：
  776.3±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (6R,7R)-4-methoxybenzyl 3-(acetoxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 在 吡啶 、 indium 、 三甲基氯硅烷 、 potassium iodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 27.0h， 生成 头孢克肟GENE杂质
  参考文献：
  名称：

  A facile synthesis of 7-amino-3-desacetoxycephalosporanic acid derivatives by indium-mediated reduction of 3-iodomethylcephems in aqueous media

  摘要：

  An efficient reductive conversion of 3-iodomethylcephalosporin and 3-acetoxymethylcephalosporin derivatives mediated by indium into the corresponding 3-methylcephems and 3-methylenecephams in moderate to good yields has been developed in an aqueous system. 3-Methylenecephams are converted into the corresponding 3-methylcephems under previously reported basic conditions quantitatively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00512-8
• 作为产物：
  描述：

  头孢洛仑 、 4-甲氧基溴苄 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 以57.5%的产率得到(6R,7R)-4-methoxybenzyl 3-(acetoxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Enzymatic Deprotection of the Cephalosporin 3′-Acetoxy Group Using Candida antarctica Lipase B

  摘要：

  Cephalosporins remain one of the most important classes of antibiotics. A useful site for derivatization involves generation of and chemistry at the 3'-hydroxymethyl position. While 3'-acetoxymethyl-substituted cephalosporins are readily available, deacetylation to access the free 3'-hydroxymethyl group is problematic when the carboxylic acid is protected as an ester. Herein we report that this important transformation has been efficiently accomplished using Candida antarctica lipase B. Although this transformation is difficult to carry out using chemical methods, the enzymatic deacetylation has been successful on gram scale, when the cephalosporin is protected as either the benzhydryl or tert-butyl esters and on the corresponding sulfoxide and sulfone of the tert-butyl ester.

  DOI：

  10.1021/jo902406b

文献信息

• Reactions of TMSI with cephalosporin esters
  作者：Rosanne Bonjouklian、Michael L. Phillips

  DOI：10.1016/s0040-4039(01)82025-6

  日期：1981.1

  The direct synthesis of 3-iodomethyl cephalosporin esters from 3-acetoxy- and 3-carbamoylmethyl analogues may be achieved using TMSI. The “one-pot” conversion of sodium cephalothin into a C-3 heterocycle-substituted cephalosporin may also be performed using TMSI-mediated chemistry.

  使用TMSI可以从3-乙酰氧基-和3-氨基甲酰基甲基类似物直接合成3-碘甲基头孢菌素酯。也可以使用TMSI介导的化学方法将头孢菌素钠“一锅”转化为C-3杂环取代的头孢菌素。