(3S,4R,5S)-3-azido-4-[dimethyl(phenyl)silyl]-5-[(1R)-1-hydroxyethyl]oxolan-2-one | 146328-53-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4R,5S)-3-azido-4-[dimethyl(phenyl)silyl]-5-[(1R)-1-hydroxyethyl]oxolan-2-one
• CAS: 146328-53-2
• 化学式: C₁₄H₁₉N₃O₃Si
• 分子量: 305.409
• InChiKey: DMKPNLQTRFXPHX-FOUMNBMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-3-azido-4-[dimethyl(phenyl)silyl]-5-[(1R)-1-hydroxyethyl]oxolan-2-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4R,5S)-3-azido-4-[dimethyl(phenyl)silyl]-5-[(1R)-1-hydroxyethyl]oxolan-2-ol
  参考文献：
  名称：

  Diastereoselectivity in the osmium tetraoxide promoted dihydroxylation of chiral (E)-crotylsilane: asymmetric synthesis of silyl-functionalized .gamma.-lactones

  摘要：

  The catalytic osmylation of enantiomerically enriched (E)-crotylsilanes (2S,3R)-1 and (2R,3R)-2 containing a homoallylic, nitrogen-bearing stereocenter proceeds with good to high levels of diastereoselection generating silyl-functionalized trans-4,5 substituted gamma-lactones 3 and 5 as the major diastereomers.

  DOI：

  10.1021/jo00054a002
• 作为产物：
  描述：

  methyl (E,2S,3S)-2-azido-3-[dimethyl(phenyl)silyl]hex-4-enoate 在 盐酸 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 作用下， 生成 (3S,4R,5S)-3-azido-4-[dimethyl(phenyl)silyl]-5-[(1R)-1-hydroxyethyl]oxolan-2-one
  参考文献：
  名称：

  Diastereoselectivity in the osmium tetraoxide promoted dihydroxylation of chiral (E)-crotylsilane: asymmetric synthesis of silyl-functionalized .gamma.-lactones

  摘要：

  The catalytic osmylation of enantiomerically enriched (E)-crotylsilanes (2S,3R)-1 and (2R,3R)-2 containing a homoallylic, nitrogen-bearing stereocenter proceeds with good to high levels of diastereoselection generating silyl-functionalized trans-4,5 substituted gamma-lactones 3 and 5 as the major diastereomers.

  DOI：

  10.1021/jo00054a002

文献信息

• Diastereoselectivity in the osmium tetraoxide promoted dihydroxylation of chiral (E)-crotylsilane: asymmetric synthesis of silyl-functionalized .gamma.-lactones
  作者：James S. Panek、Jing Zhang

  DOI：10.1021/jo00054a002

  日期：1993.1

  The catalytic osmylation of enantiomerically enriched (E)-crotylsilanes (2S,3R)-1 and (2R,3R)-2 containing a homoallylic, nitrogen-bearing stereocenter proceeds with good to high levels of diastereoselection generating silyl-functionalized trans-4,5 substituted gamma-lactones 3 and 5 as the major diastereomers.