(1S,2S,7R,8S,8aR)-(-)-1,2-dibenzyloxy-7,8-dihydroxy-5-oxoindolizidine | 355145-82-3

• 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,2S,7R,8S,8aR)-(-)-1,2-dibenzyloxy-7,8-dihydroxy-5-oxoindolizidine
• 英文别名: (1S,2S,7R,8S,8aR)-7,8-dihydroxy-1,2-bis(phenylmethoxy)-2,3,6,7,8,8a-hexahydro-1H-indolizin-5-one
• CAS: 355145-82-3
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: KNBSZPBGZVDERN-HVYFLLBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,7R,8S,8aR)-(-)-1,2-dibenzyloxy-7,8-dihydroxy-5-oxoindolizidine 在 10percent Pd on carbon 盐酸 、 dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 (1S,2S,7R,8S,8aR)-(-)-1,2,7,8-tetrahydroxyindolizidine
  参考文献：
  名称：

  Stereoisomeric Sugar-Derived Indolizines as Versatile Building Blocks:  Synthesis of Enantiopure Di- and Tetrahydroxyindolizidines

  摘要：

  The synthesis of the sugar-derived (1S,2R,8aR)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5- oxoindolizine (8) and by analogy of the corresponding stereoisomers ent-8 and ent-7, an epimer at C-2 of ent-8, has been accomplished in a straightforward manner. The carbon-carbon double bond and the carbonyl functionalities on the six-membered ring make these nitrogen-containing heterocycles useful building blocks for the efficient preparation of a variety of enantiopure polyhydroxylated indolizidines of interest for their glycosidase inhibitory activity. We report here the synthesis of 2,8a-diepilentiginosine 12 from 8 and the preparation of stereoisomeric 1,2,7,8-tetrahydroxyindolizidines 9-11 performed by OsO4-catalyzed double bond syn dihydroxylation of 7 and 8, followed by deoxygenation of the amide group.

  DOI：

  10.1021/jo0016428
• 作为产物：
  描述：

  (1S,2S,8aR)-1,2-Bis-benzyloxy-2,3,6,8a-tetrahydro-1H-indolizin-5-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 36.0h， 以65%的产率得到(1S,2S,7R,8S,8aR)-(-)-1,2-dibenzyloxy-7,8-dihydroxy-5-oxoindolizidine
  参考文献：
  名称：

  Stereoisomeric Sugar-Derived Indolizines as Versatile Building Blocks:  Synthesis of Enantiopure Di- and Tetrahydroxyindolizidines

  摘要：

  The synthesis of the sugar-derived (1S,2R,8aR)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5- oxoindolizine (8) and by analogy of the corresponding stereoisomers ent-8 and ent-7, an epimer at C-2 of ent-8, has been accomplished in a straightforward manner. The carbon-carbon double bond and the carbonyl functionalities on the six-membered ring make these nitrogen-containing heterocycles useful building blocks for the efficient preparation of a variety of enantiopure polyhydroxylated indolizidines of interest for their glycosidase inhibitory activity. We report here the synthesis of 2,8a-diepilentiginosine 12 from 8 and the preparation of stereoisomeric 1,2,7,8-tetrahydroxyindolizidines 9-11 performed by OsO4-catalyzed double bond syn dihydroxylation of 7 and 8, followed by deoxygenation of the amide group.

  DOI：

  10.1021/jo0016428

文献信息

• Stereoisomeric Sugar-Derived Indolizines as Versatile Building Blocks:  Synthesis of Enantiopure Di- and Tetrahydroxyindolizidines
  作者：Claudio Paolucci、Lucia Mattioli

  DOI：10.1021/jo0016428

  日期：2001.7.1

  The synthesis of the sugar-derived (1S,2R,8aR)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5- oxoindolizine (8) and by analogy of the corresponding stereoisomers ent-8 and ent-7, an epimer at C-2 of ent-8, has been accomplished in a straightforward manner. The carbon-carbon double bond and the carbonyl functionalities on the six-membered ring make these nitrogen-containing heterocycles useful building blocks for the efficient preparation of a variety of enantiopure polyhydroxylated indolizidines of interest for their glycosidase inhibitory activity. We report here the synthesis of 2,8a-diepilentiginosine 12 from 8 and the preparation of stereoisomeric 1,2,7,8-tetrahydroxyindolizidines 9-11 performed by OsO4-catalyzed double bond syn dihydroxylation of 7 and 8, followed by deoxygenation of the amide group.