((1R,2S)-1-Benzyloxymethyl-2-methyl-but-3-enyl)-carbamic acid tert-butyl ester | 477332-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((1R,2S)-1-Benzyloxymethyl-2-methyl-but-3-enyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2R,3S)-3-methyl-1-phenylmethoxypent-4-en-2-yl]carbamate
• CAS: 477332-07-3
• 化学式: C₁₈H₂₇NO₃
• 分子量: 305.417
• InChiKey: GGZLQRFMULXFJN-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((1R,2S)-1-Benzyloxymethyl-2-methyl-but-3-enyl)-carbamic acid tert-butyl ester 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 三氯化硼 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 Benzoic acid (2R,3S)-2-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-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：

  甲基三苯基溴化膦 、 ((1R,2R)-1-Benzyloxymethyl-2-methyl-3-oxo-propyl)-carbamic acid tert-butyl ester 在 正丁基锂 作用下， 生成 ((1R,2S)-1-Benzyloxymethyl-2-methyl-but-3-enyl)-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

文献信息

• Asymmetric synthesis of a C1C19 fragment of ulapualide A
  作者：Cassandra A. Celatka、James S. Panek

  DOI：10.1016/s0040-4039(02)01553-8

  日期：2002.9

  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.