methyl (2R,3R)-α-azido-β-(dimethylphenylsilyl)-(E)-hex-4-enoate | 136824-22-1

• 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: methyl (2R,3R)-α-azido-β-(dimethylphenylsilyl)-(E)-hex-4-enoate
• 英文别名: (2R,3R)-Methyl 2-azido-3-(dimethylphenylsilyl)-(E)-hex-4-enoate；methyl (E,2R,3R)-2-azido-3-[dimethyl(phenyl)silyl]hex-4-enoate
• CAS: 136824-22-1
• 化学式: C₁₅H₂₁N₃O₂Si
• 分子量: 303.436
• InChiKey: IVYGGYULHXTPKQ-JEELVDDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R)-α-azido-β-(dimethylphenylsilyl)-(E)-hex-4-enoate 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (E)-(2R,3R)-2-Amino-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester
  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：

  4-己烯酸,3-(二甲基苯基甲硅烷基)-,甲基酯,(3S,4E)- 在 正丁基锂 、 2,4,6-三异丙基苯磺酰叠氮化物 、 溶剂黄146 、 二异丙胺 作用下， 生成 methyl (2R,3R)-α-azido-β-(dimethylphenylsilyl)-(E)-hex-4-enoate 、 methyl (2S,3R)-α-azido-β-(dimethylphenylsilyl)-(E)-hex-4-enoate
  参考文献：
  名称：

  Diastereoselective electrophilic addition reactions to chiral .beta.-dimethylphenylsilyl ester enolates. Synthesis of 2,3-anti-.alpha.-substituted-.beta.-silyl-(E)-hex-4-enoates

  摘要：

  DOI：

  10.1021/jo00026a030

文献信息

• Sequential diastereoselective addition and allylic azide isomerization of syn- and anti-.alpha.-azido-.beta.-(dimethylphenylsilyl)-(E)-hex-4-enoates with acetals: asymmetric synthesis of .gamma.-hydroxy-.alpha.-amino acid synthons
  作者：James S. Panek、Michael Yang、Itzhak Muler

  DOI：10.1021/jo00041a002

  日期：1992.7

  syn- and anti-methyl alpha-azido-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates (2R,3R)-1a and (2S,3R)-1b undergo highly diastereo- and enantioselective addition reactions with oxonium ions catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) to generate alpha-azido-beta,gamma-unsaturated esters 2, with well-defined 1,4- and 1,5-stereochemical relationships, and a subsequent stereospecific allylic azide isomerization generated 1,3-azido ethers 3, synthetic equivalents of gamma-hydroxy-alpha-amino acids.
• Diastereoselective electrophilic addition reactions to chiral .beta.-dimethylphenylsilyl ester enolates. Synthesis of 2,3-anti-.alpha.-substituted-.beta.-silyl-(E)-hex-4-enoates
  作者：James S. Panek、Richard Beresis、Feng Xu、Michael Yang

  DOI：10.1021/jo00026a030

  日期：1991.12
• 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.