((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethyl)-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester | 356785-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: ((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethyl)-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester
• 英文别名: N-[(2R,4aR,6S,7R,8R,8aS)-8-[[1,1-diethoxyethyl(ethoxy)phosphoryl]methoxy]-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 356785-89-2
• 化学式: C₃₁H₄₄NO₁₀P
• 分子量: 621.665
• InChiKey: MSBFQVDOQFALBY-ZMTUDJBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  120.01
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethyl)-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester 在 三甲基氯硅烷 、 TEA 、 水 作用下， 以 氯仿 为溶剂， 反应 1.58h， 生成 2-[((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethyl)-ethoxy-phosphinoylmethyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Inhibitors of the bacterial cell wall biosynthesis enzyme MurC

  摘要：

  A series of phosphinate transition-state analogues of the L-alanine adding enzyme (MurC) of bacterial peptidoglycan biosynthesis was prepared and tested as inhibitors of the Escherichia coli enzyme. Compound 4 was identified as a potent inhibitor of MurC from Escherichia coli with an IC50 Of 49 nM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00251-7
• 作为产物：
  描述：

  ethyl (hydroxymethyl)(1,1-diethoxyethyl)phosphinate 在 sodium hydride 、 二异丙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 ((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethyl)-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester
  参考文献：
  名称：

  Inhibitors of the bacterial cell wall biosynthesis enzyme MurC

  摘要：

  A series of phosphinate transition-state analogues of the L-alanine adding enzyme (MurC) of bacterial peptidoglycan biosynthesis was prepared and tested as inhibitors of the Escherichia coli enzyme. Compound 4 was identified as a potent inhibitor of MurC from Escherichia coli with an IC50 Of 49 nM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00251-7

文献信息

• Inhibitors of the bacterial cell wall biosynthesis enzyme MurC
  作者：Folkert Reck、Stephen Marmor、Stewart Fisher、Mark A. Wuonola

  DOI：10.1016/s0960-894x(01)00251-7

  日期：2001.6

  A series of phosphinate transition-state analogues of the L-alanine adding enzyme (MurC) of bacterial peptidoglycan biosynthesis was prepared and tested as inhibitors of the Escherichia coli enzyme. Compound 4 was identified as a potent inhibitor of MurC from Escherichia coli with an IC50 Of 49 nM. (C) 2001 Elsevier Science Ltd. All rights reserved.