3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)pyrrolidin-2-yl)propionic acid ethyl ester | 948897-77-6

• 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: 3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)pyrrolidin-2-yl)propionic acid ethyl ester
• CAS: 948897-77-6
• 化学式: C₃₉H₄₅NO₆
• 分子量: 623.789
• InChiKey: CGBIJOOYVLPZKN-XNVAUQMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  46.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)pyrrolidin-2-yl)propionic acid ethyl ester 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 15.0h， 以87%的产率得到3-((2S,3S,4S,5S)-3,4-dihydroxy-5-((S)-1,2-dihydroxyethyl)-pyrrolidin-2-yl)propanoic acid ethyl ester hydrochloride salt
  参考文献：
  名称：

  Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors

  摘要：

  The synthesis of 1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols involving nitrone umpolung is described. The SmI2-induced key coupling proved highly stereoselective in favor of the beta-C-substituted products bearing a three-carbon chain at the pseudoanomeric position. Pyrrolidines 9 and 10, as well as the bicyclic compounds 8 and 11, exhibit weak inhibition of the activity of the UDP-galactopyranose mutase from Escherichia coli. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.059
• 作为产物：
  描述：

  3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)-1-hydroxy-pyrrolidin-2-yl)propionic acid ethyl ester 在 samarium diiodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以68%的产率得到3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)pyrrolidin-2-yl)propionic acid ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors

  摘要：

  The synthesis of 1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols involving nitrone umpolung is described. The SmI2-induced key coupling proved highly stereoselective in favor of the beta-C-substituted products bearing a three-carbon chain at the pseudoanomeric position. Pyrrolidines 9 and 10, as well as the bicyclic compounds 8 and 11, exhibit weak inhibition of the activity of the UDP-galactopyranose mutase from Escherichia coli. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.059