[(1R,2S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester | 477332-16-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(1R,2S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester
• CAS: 477332-16-4
• 化学式: C₂₇H₄₁NO₄Si
• 分子量: 471.712
• InChiKey: FFSCEKMETVUSQF-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(1R,2S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Benzoic acid (2R,3S)-5-(tert-butyl-diphenyl-silanyloxy)-2-[(2'-methoxymethoxymethyl-[2,4']bioxazolyl-4-carbonyl)-amino]-3-methyl-pentyl ester
  参考文献：
  名称：

  Asymmetric synthesis of a C1C19 fragment of ulapualide A

  摘要：

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01553-8
• 作为产物：
  描述：

  [(1R,2S)-1-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-butyl]-carbamic acid tert-butyl ester 在 三氯化硼 作用下， 以 甲苯 为溶剂， 以82%的产率得到[(1R,2S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric synthesis of a C1C19 fragment of ulapualide A

  摘要：

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01553-8