(1S,2R,8aR)-(+)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5-oxoindolizine | 355145-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,8aR)-(+)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5-oxoindolizine
• 英文别名: (3aR,9aR,9bS)-2,2-dimethyl-4,7,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one
• CAS: 355145-76-5
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: SKWANCUVZHUHIT-MRTMQBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,8aR)-(+)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5-oxoindolizine 在 10percent Pd on carbon 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,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)-4-ethenyl-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 在 Grubbs catalyst first generation 、 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 1.0h， 生成 (1S,2R,8aR)-(+)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5-oxoindolizine
  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

• Stereoselective Michael Addition of Carbon-, Nitrogen-, Oxygen-, and Sulfur-Centered Nucleophiles on Enantiopure Hydroxylated 6,7-Dehydro-5-oxoindolizidine. Synthesis of Carbon- or Hetero-7-Substituted Swainsonine Analogues
  作者：Alessandro Tinarelli、Claudio Paolucci

  DOI：10.1021/jo060511p

  日期：2006.8.1

  Enantiopure alpha beta-unsaturated delta-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines: (7R)-7-amino-8-deoxyswainsonine 3 and (7R)-7-acetylaminoswainsonine 4.
• 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.