(R)-((5R,6S,7R,7aS)-6,7-Dihydroxy-hexahydro-pyrrolo[2,1-b]thiazol-5-yl)-hydroxy-acetic acid methyl ester | 681033-58-9

• 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: (R)-((5R,6S,7R,7aS)-6,7-Dihydroxy-hexahydro-pyrrolo[2,1-b]thiazol-5-yl)-hydroxy-acetic acid methyl ester
• 英文别名: methyl (2R)-2-[(5R,6S,7R,7aS)-6,7-dihydroxy-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b][1,3]thiazol-5-yl]-2-hydroxyacetate
• CAS: 681033-58-9
• 化学式: C₉H₁₅NO₅S
• 分子量: 249.288
• InChiKey: DFFAUKBFHRHPLB-UOLFYFMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-((5R,6S,7R,7aS)-6,7-Dihydroxy-hexahydro-pyrrolo[2,1-b]thiazol-5-yl)-hydroxy-acetic acid methyl ester 在 ammonium hydroxide 作用下， 反应 8.0h， 以73%的产率得到(R)-2-((5R,6S,7R,7aS)-6,7-Dihydroxy-hexahydro-pyrrolo[2,1-b]thiazol-5-yl)-2-hydroxy-acetamide
  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：

  Trifluoro-methanesulfonic acid (6S,7S,8S,9R,9aR)-7,8,9-trihydroxy-5-oxo-octahydro-thiazolo[3,2-a]azepin-6-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到(R)-((5R,6S,7R,7aS)-6,7-Dihydroxy-hexahydro-pyrrolo[2,1-b]thiazol-5-yl)-hydroxy-acetic 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