(2S,3R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester | 216062-13-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester
• CAS: 216062-13-4
• 化学式: C₃₃H₄₁NO₅Si
• 分子量: 559.778
• InChiKey: MBWQVXHXWFDMPW-YPKYBTACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester 在 palladium hydroxide - carbon sodium tetrahydroborate 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (2S,4S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-((R)-1,2-diphenyl-ethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric synthesis of 1-Boc-3- and 4-hydroxypyrrolidines

  摘要：

  Lewis Acid-mediated coupling reactions of (5R, 6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine (2a) with allylsilanes (3a-d) proceeded to give the coupling products (4a-b) with moderate to good stereoselectivity. The coupling products (4a-b) were effectively converted into 1-Boc-3-and 4-hydroxypyrrolidines (8a, syn-b, and c). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00807-2
• 作为产物：
  描述：

  (2S,3R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到(2S,3R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  Asymmetric synthesis of 1-Boc-3- and 4-hydroxypyrrolidines

  摘要：

  Lewis Acid-mediated coupling reactions of (5R, 6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine (2a) with allylsilanes (3a-d) proceeded to give the coupling products (4a-b) with moderate to good stereoselectivity. The coupling products (4a-b) were effectively converted into 1-Boc-3-and 4-hydroxypyrrolidines (8a, syn-b, and c). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00807-2