(1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyhexahydroindolizin-3-one | 89651-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyhexahydroindolizin-3-one
• 英文别名: (1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• CAS: 89651-37-6
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: QFHJZLCBUYXRFD-OASCRQMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyhexahydroindolizin-3-one 在 二异丁基氢化铝 作用下， 生成 栗精胺
  参考文献：
  名称：

  Total syntheses of (+)-castanospermine and (+)-deoxynojirimycin

  摘要：

  DOI：

  10.1016/s0040-4039(00)99830-7
• 作为产物：
  描述：

  栗精胺 在 吡啶 、 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.08h， 生成 (1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyhexahydroindolizin-3-one
  参考文献：
  名称：

  Novel Synthesis of Castanospermine and 1-Epicastanospermine

  摘要：

  Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates lid the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.

  DOI：

  10.1021/ol0508577

文献信息

• The chemistry of castanospermine. Direct oxidation of the tetraacetate to the corresponding γ-lactam
  作者：Richard H Furneaux、Graeme J Gainsford、Jennifer M Mason、Peter C Tyler

  DOI：10.1016/j.carres.2004.05.006

  日期：2004.7

  From the products of oxidation of tetra-O-acetylcastanospermine (2) with N-bromosuccinimide, only the gamma-lactam 11 was isolated (19%). Treatment of this lactam with DBU in dichloromethane afforded the elimination product 12, while deacetylation with sodium methoxide in methanol gave tetraol 13 together with diene 14. The X-ray crystal structure of compound 13 is reported.

  从N-溴代琥珀酰亚胺氧化四-O-乙酰基castanospermine（2）的产物中，仅分离出γ-内酰胺11（19％）。用DBU在二氯甲烷中处理该内酰胺，得到消除产物12，而在甲醇中用甲醇钠脱乙酰，得到四醇13和二烯14。报道了化合物13的X射线晶体结构。
• Novel Synthesis of Castanospermine and 1-Epicastanospermine
  作者：Linda Cronin、Paul V. Murphy

  DOI：10.1021/ol0508577

  日期：2005.6.1

  Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates lid the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.
• Total syntheses of (+)-castanospermine and (+)-deoxynojirimycin
  作者：Ronald C. Bernotas、Bruce Ganem

  DOI：10.1016/s0040-4039(00)99830-7

  日期：1984.1