6,7-Diepicastanospermine | 130983-46-9

• 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: 6,7-Diepicastanospermine
• 英文别名: (1S,6R,7S,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol
• CAS: 130983-46-9
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: JDVVGAQPNNXQDW-FMGWEMOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  栗精胺 在 吡啶 、 氢氧化钾 、 硫酸 、 三正丁基甲氧基锡 作用下， 以 四氢呋喃 、 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 6,7-Diepicastanospermine
  参考文献：
  名称：

  粟精胺的化学，第一部分：C-6的合成修饰

  摘要：

  概述了粟精胺的选择性功能化的方法学，该方法学允许合成许多在C-6处选择性修饰的类似物。还从粟精胺合成了Australine和一些australine类似物。

  DOI：

  10.1016/s0040-4020(01)85075-4

文献信息

• An azide-diene cycloaddition approach to indolizidine alkaloids. An enantioselective synthesis of 67-diepicastanospermine
  作者：No-Soo Kim、Chul Hyun Kang、Jin Kun Cha

  DOI：10.1016/s0040-4039(00)73217-5

  日期：1994.5

  A short, enantioselective synthesis of 6,7-diepicastanospermine (4) has been achieved by an intramolecular azide-diene 1,3-dipolar cycloaddition, followed by ring-opening of the vinylaziridine 6 and subsequent dihydroxylation.

  通过分子内叠氮化物-二烯1，3-偶极环加成，随后乙烯基氮丙啶6的开环和随后的二羟基化，实现了短的对映选择性合成6,7-di Epi Castanospermine（4）。
• A chemoenzymatic synthesis of (+)-castanospermine
  作者：Rojeev Bhide、Reza Mortezaei、A. Scilimati、Charles J. Sih

  DOI：10.1016/s0040-4039(00)97743-8

  日期：1990.1
• Stereoselective Synthesis of Polyhydroxylated Indolizidines from γ-Hydroxy α,β-Unsaturated Sulfones
  作者：Juan C. Carretero、Ramón Gómez Arrayás

  DOI：10.1021/jo972167p

  日期：1998.5.1

  The polyhydroxylated indolizidines castanospermine and swainsonine as well as some of their stereoisomers are powerful glycosidase inhibitors. An efficient and stereochemically flexible synthesis of racemic 1,7,8-trihydroxylated and 1,6,7,8-tetrahydroxylated indolizidines (castanospermine stereoisomers) from readily available N-substituted gamma-oxygenated alpha,beta-unsaturated sulfones 3 and 4 has been developed. The construction of the bicyclic skeleton of 1-hydroxyindolizidine has been accomplished by intramolecular conjugate addition of the nitrogen moiety of 3 and 4 to the alpha,beta-unsaturated sulfone unit to give the pyrrolidine intermediates 5 and 6, followed by formation of the C(7)-C(8) bond by intramolecular acylation (or alkylation) of the alpha-sulfonyl carbanion. The stereoselectivity of the pyrrolidine synthesis was highly dependent on the bulkiness of the gamma-oxygenated function; thus, the free alcohols gave predominantly cis-pyrrolidines while the OTIPS derivatives led to the trans isomers. After straightforward functional group transformations, the removal of the sulfonyl group at C(8) either by Julia reaction or by basic elimination (depending on the substrate used) afforded the key C(7)C(8) unsaturated indolizidines 10, 22, 30, and 31, whose stereoselective dihydroxylations with OsO4 gave a variety of cis C(1)C(8a) and-trans C(1)C(8a) trihydroxylated and tetrahydroxylated indolizidines, among which (+/-)-1,7-di-epi-castanospermine and (+/-)-1,8-di-epi-castanospermine have been reported for the first time.
• BHIDE, ROJEEV;MORTEZAEI, REZA;SCILIMATI, A.;SIH, CHARLES J., TETRAHEDRON LETT., 31,(1990) N4, C. 4827-4830
  作者：BHIDE, ROJEEV、MORTEZAEI, REZA、SCILIMATI, A.、SIH, CHARLES J.

  DOI：——

  日期：——
• The chemistry of castanospermine, part I: synthetic modifications at C-6
  作者：Richard H. Furneaux、Graeme J. Gainsford、Jennifer M. Manson、Peter C. Tyler

  DOI：10.1016/s0040-4020(01)85075-4

  日期：1994.2

  Methodology for the selective functionalisation of castanospermine is outlined which has allowed the synthesis of a number of analogues selectively modified at C-6. Australine and some australine analogues have also been synthesized from castanospermine.

  概述了粟精胺的选择性功能化的方法学，该方法学允许合成许多在C-6处选择性修饰的类似物。还从粟精胺合成了Australine和一些australine类似物。