1,6,7,8-tetrahydroxy-7,8-O-isopropylideneindolizidine | 133576-14-4

• 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: 1,6,7,8-tetrahydroxy-7,8-O-isopropylideneindolizidine
• 英文别名: (3aR,4R,9S,9aR,9bR)-2,2-dimethyl-3a,4,5,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-g]indolizine-4,9-diol
• CAS: 133576-14-4
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: RWMVJSHRXXDECP-VAPHQMJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.68
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.16
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,6,7,8-tetrahydroxy-7,8-O-isopropylideneindolizidine 在 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以84%的产率得到(1S,6R,7R,8R,8aR)-1,2,3,5,6,7,8,8a-八氢吲嗪-1,6,7,8-四醇
  参考文献：
  名称：

  2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-6-epicastanospermine

  摘要：

  D-2-Amino-2-deoxyglucosaminic acid, obtained from D-glucosamine, and a D-2-amino-2-deoxymannosaminic acid derivative, obtained from D-glucono-delta-lactone, were derivatized and converted to the corresponding configurationally stable aldehydes. The N-(9-phenylfuoren-9-yl)-protected mannosamine derivative was readily transformed into a variety of configurationally stable alpha-amino ketones, thus providing convenient and versatile chiral educts. These educts may be envisaged as derivable from polyhydroxy alpha-amino acids. Examples of the utility of these chiral educts are provided by the efficient conversion of a D-mannosaminic acid derivative into the polyhydroxy indolizidine alkaloids (+)-castanospermine and (+)-6-epicastanospermine.

  DOI：

  10.1021/jo00011a047
• 作为产物：
  描述：

  2-(1',2'-O-isopropylidene-4'-O-tosyl-1',2',3',4'-tetrahydroxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 甲醇 为溶剂， 以92%的产率得到1,6,7,8-tetrahydroxy-7,8-O-isopropylideneindolizidine
  参考文献：
  名称：

  2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-6-epicastanospermine

  摘要：

  D-2-Amino-2-deoxyglucosaminic acid, obtained from D-glucosamine, and a D-2-amino-2-deoxymannosaminic acid derivative, obtained from D-glucono-delta-lactone, were derivatized and converted to the corresponding configurationally stable aldehydes. The N-(9-phenylfuoren-9-yl)-protected mannosamine derivative was readily transformed into a variety of configurationally stable alpha-amino ketones, thus providing convenient and versatile chiral educts. These educts may be envisaged as derivable from polyhydroxy alpha-amino acids. Examples of the utility of these chiral educts are provided by the efficient conversion of a D-mannosaminic acid derivative into the polyhydroxy indolizidine alkaloids (+)-castanospermine and (+)-6-epicastanospermine.

  DOI：

  10.1021/jo00011a047

文献信息

• GERSPACHER, MARC;RAPOPORT, HENRY, J. ORG. CHEM., 56,(1991) N1, C. 3700-3706
  作者：GERSPACHER, MARC、RAPOPORT, HENRY

  DOI：——

  日期：——