(3aS,4R,6aR)-4-ethenyl-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole | 355145-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,6aR)-4-ethenyl-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
• CAS: 355145-96-9
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: HJPNJPQMJZNKLY-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6aR)-4-ethenyl-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 在 10percent Pd on carbon Grubbs catalyst first generation 、 dimethyl sulfide borane 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 苯 为溶剂， 反应 4.0h， 生成 (1S,2R,8aR)-(-)-1,2-di-O-isopropylidenindolizidine
  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：

  (3aS,4R,6aR)-2,2-Dimethyl-4-vinyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester 在 碘代三甲硅烷 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 (3aS,4R,6aR)-4-ethenyl-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
  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