(2S,3R,6S)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester | 216062-11-2

• 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-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester
• 英文别名: benzyl (2S,3R,6S)-6-[(2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxypropyl]-2,3-diphenylmorpholine-4-carboxylate
• CAS: 216062-11-2
• 化学式: C₃₃H₄₃NO₅Si
• 分子量: 561.794
• InChiKey: RFZQGBDHWPRZLT-ITGKQZKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,6S)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester 在 palladium hydroxide - carbon 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 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,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2(2-propenyl)-1,2,5,6-tetrahydro-4H-1,4-oxazine 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 63.0h， 生成 (2S,3R,6S)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-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

文献信息

• Asymmetric synthesis of 1-Boc-3- and 4-hydroxypyrrolidines
  作者：Yutaka Aoyagi、Robert M. Williams

  DOI：10.1016/s0040-4020(98)00807-2

  日期：1998.10

  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.