S-tert-butyl (2R*,3S*)-2-ethyl-3-hydroxy-5-(trimethylsilyl)pent-4-ynethioate | 139472-45-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-tert-butyl (2R*,3S*)-2-ethyl-3-hydroxy-5-(trimethylsilyl)pent-4-ynethioate
• 英文别名: anti-S-tert-Butyl-2-ethyl-3-hydroxy-5-(trimethylsilyl)-4-pentynethioate；S-tert-butyl (2R,3S)-2-ethyl-3-hydroxy-5-trimethylsilylpent-4-ynethioate
• CAS: 139472-45-0；139472-48-3；148117-68-4；148117-72-0
• 化学式: C₁₄H₂₆O₂SSi
• 分子量: 286.511
• InChiKey: MFGPZFUBLGDWET-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-tert-butyl (2R*,3S*)-2-ethyl-3-hydroxy-5-(trimethylsilyl)pent-4-ynethioate 在 三氯硅烷 、 三乙胺 作用下， 以 苯 为溶剂， 生成 S-tert-Butyl (2S,3R)-2-ethyl-3-hydroxy-5-(trimethylsilyl)-4-pentynethioate
  参考文献：
  名称：

  An efficient method for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates: a highly stereoselective total synthesis of (+)-bengamide E1

  摘要：

  A novel. procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation. Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.

  DOI：

  10.1021/jo00123a030
• 作为产物：
  描述：

  S-tert-Butyl (2R,3S)-2-ethyl-3-<<<(S)-1-phenylethyl>amino>carboxy>-5-(trimethylsilyl)-4-pentynethioate 在 三氯硅烷 、 三乙胺 作用下， 以 苯 为溶剂， 以83%的产率得到S-tert-butyl (2R*,3S*)-2-ethyl-3-hydroxy-5-(trimethylsilyl)pent-4-ynethioate
  参考文献：
  名称：

  An efficient method for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates: a highly stereoselective total synthesis of (+)-bengamide E1

  摘要：

  A novel. procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation. Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.

  DOI：

  10.1021/jo00123a030

文献信息

• A highly diastereoselective aldol reaction of dicobalt hexacarbonyl propynal complex and uncomplexed propynal: A stereoselective divergent synthesis of (±)-PS-5 and (±)-6-Epi-PS-5
  作者：Chisato Mukai、Osamu Kataoka、Miyoji Hanaoka

  DOI：10.1016/0040-4039(91)80532-b

  日期：1991.12

  The aldol reaction of cobalt complexes propynal 1 with O-silyl ketene O,S-acetals 3 gave the syn-products exclusively, while the uncomplexed propynal 2, the corresponding anti-compounds. A successful application of these stereoselective reactions to a synthesis of (±)-PS-5 and (±)-6-epi-PS-5 is described.

  钴配合物丙醛1与O-甲硅烷基烯酮O，S-乙缩醛3的醛醇缩合反应仅产生合成产物，而未配合的丙醛2即相应的反化合物。描述了将这些立体选择性反应成功应用于（±）-PS-5和（±）-6-epi-PS-5的合成。
• Mukai, Chisato; Kataoka, Osamu; Hanaoka, Miyoji, Journal of the Chemical Society. Perkin transactions I, 1993, # 5, p. 563 - 572
  作者：Mukai, Chisato、Kataoka, Osamu、Hanaoka, Miyoji

  DOI：——

  日期：——
• An efficient method for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates: a highly stereoselective total synthesis of (+)-bengamide E1
  作者：Chisato Mukai、Osamu Kataoka、Miyoji Hanaoka

  DOI：10.1021/jo00123a030

  日期：1995.9

  A novel. procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation. Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.