(3R,5R,6S,7R,7aS)-6,7-Dihydroxy-5-((R)-hydroxy-methoxycarbonyl-methyl)-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid methyl ester | 681033-50-1

• 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: (3R,5R,6S,7R,7aS)-6,7-Dihydroxy-5-((R)-hydroxy-methoxycarbonyl-methyl)-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid methyl ester
• 英文别名: methyl (3R,5R,6S,7R,7aS)-6,7-dihydroxy-5-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b][1,3]thiazole-3-carboxylate
• CAS: 681033-50-1
• 化学式: C₁₁H₁₇NO₇S
• 分子量: 307.324
• InChiKey: GOGKIILDNSLOTF-ARADLNFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R,5R,6S,7R,7aS)-6,7-Dihydroxy-5-((R)-hydroxy-methoxycarbonyl-methyl)-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以92%的产率得到(3R,5R,6S,7R,7aS)-5-((R)-Carboxy-hydroxy-methyl)-6,7-dihydroxy-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of hydroxylated hexahydropyrrolo[2,1-b]thiazoles

  摘要：

  An unexpected ring contraction of 7,5-fused bicyclic thiazolidinelactams yields hexahydropyrrolo[2,1-b]thiazoles in a single synthetic step. Three stereocentres are inverted along the highly stereoselective reaction path. The title compounds are further transformed into thio-analogues of polyhydroxylated pyrrolizidine alkaloids. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.016
• 作为产物：
  描述：

  (3R,6S,7S,8S,9R,9aR)-7,8,9-Trihydroxy-5-oxo-6-trifluoromethanesulfonyloxy-octahydro-thiazolo[3,2-a]azepine-3-carboxylic acid ethyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到(3R,5R,6S,7R,7aS)-6,7-Dihydroxy-5-((R)-hydroxy-methoxycarbonyl-methyl)-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of hydroxylated hexahydropyrrolo[2,1-b]thiazoles

  摘要：

  An unexpected ring contraction of 7,5-fused bicyclic thiazolidinelactams yields hexahydropyrrolo[2,1-b]thiazoles in a single synthetic step. Three stereocentres are inverted along the highly stereoselective reaction path. The title compounds are further transformed into thio-analogues of polyhydroxylated pyrrolizidine alkaloids. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.016

文献信息

• Synthesis of hydroxylated hexahydropyrrolo[2,1-b]thiazoles
  作者：Karoly Agoston、Armin Geyer

  DOI：10.1016/j.tetlet.2004.01.016

  日期：2004.2

  An unexpected ring contraction of 7,5-fused bicyclic thiazolidinelactams yields hexahydropyrrolo[2,1-b]thiazoles in a single synthetic step. Three stereocentres are inverted along the highly stereoselective reaction path. The title compounds are further transformed into thio-analogues of polyhydroxylated pyrrolizidine alkaloids. (C) 2004 Elsevier Ltd. All rights reserved.