S-tert-Butyl (2R,3S)-2-(benzyloxy)-3-<<<(R)-1-(naphtyl)ethyl>amino>carboxy>-6-methyl-4-heptynethioate | 171622-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S-tert-Butyl (2R,3S)-2-(benzyloxy)-3-<<<(R)-1-(naphtyl)ethyl>amino>carboxy>-6-methyl-4-heptynethioate
• 英文别名: S-tert-butyl (2R,3S)-6-methyl-3-[[(1R)-1-naphthalen-1-ylethyl]carbamoyloxy]-2-phenylmethoxyhept-4-ynethioate
• CAS: 171622-71-2
• 化学式: C₃₂H₃₇NO₄S
• 分子量: 531.716
• InChiKey: ZJAIZEAHXHMIIZ-LDVROUIZSA-N

物化性质

• 沸点：
  672.4±55.0 °C(predicted)
• 密度：
  1.148±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-tert-Butyl (2R,3S)-2-(benzyloxy)-3-<<<(R)-1-(naphtyl)ethyl>amino>carboxy>-6-methyl-4-heptynethioate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三氯硅烷 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 生成 (E,2S,3S)-1-[tert-butyl(dimethyl)silyl]oxy-6-methyl-2-phenylmethoxyhept-4-en-3-ol
  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 2-(benzyloxy)ethanethioate 生成 S-tert-Butyl (2R,3S)-2-(benzyloxy)-3-<<<(R)-1-(naphtyl)ethyl>amino>carboxy>-6-methyl-4-heptynethioate
  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

• 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.