tert-butyl ((2S,3R)-3-((benzyloxy)carbonyl)amino-2-(tert-butyldimethylsilyl)oxybutyl)(methyl)carbamate | 1326726-96-8

• 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: tert-butyl ((2S,3R)-3-((benzyloxy)carbonyl)amino-2-(tert-butyldimethylsilyl)oxybutyl)(methyl)carbamate
• 英文别名: tert-butyl N-[(2S,3R)-2-[tert-butyl(dimethyl)silyl]oxy-3-(phenylmethoxycarbonylamino)butyl]-N-methylcarbamate
• CAS: 1326726-96-8
• 化学式: C₂₄H₄₂N₂O₅Si
• 分子量: 466.693
• InChiKey: QUIBLRWZULUPCD-QUCCMNQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(N-Boc-N-甲基氨基)乙醇 在 2,6-二甲基吡啶 、 甲醇 、 草酰氯 、 三氟甲磺酸二丁硼 、 叠氮磷酸二苯酯 、 双氧水 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 25.5h， 生成 tert-butyl ((2S,3R)-3-((benzyloxy)carbonyl)amino-2-(tert-butyldimethylsilyl)oxybutyl)(methyl)carbamate
  参考文献：
  名称：

  Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions

  摘要：

  Orthogonally protected chiral beta-hydroxy-gamma-amino acids can be accessed in >100 g quantities from readily available starting materials and reagents in three to four steps. These chiral synthons contain two adjacent stereocenters along with suitably protected functional groups (O-TBS, N-Boc) for downstream reactivity. Implementation of two existing aldol technologies allows rapid access to all possible stereo-isomers of 1. The guiding principles during reaction optimization were reaction scalability and operational efficiency. Conversion of the amino acids to a variety of chiral building blocks in one to two steps demonstrates their synthetic utility. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.043

文献信息

• Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions
  作者：Bhaumik A. Pandya、Sivaraman Dandapani、Jeremy R. Duvall、Ann Rowley、Carol A. Mulrooney、Troy Ryba、Michael Dombrowski、Marie Harton、Damian W. Young、Lisa A. Marcaurelle

  DOI：10.1016/j.tet.2011.06.043

  日期：2011.8

  Orthogonally protected chiral beta-hydroxy-gamma-amino acids can be accessed in >100 g quantities from readily available starting materials and reagents in three to four steps. These chiral synthons contain two adjacent stereocenters along with suitably protected functional groups (O-TBS, N-Boc) for downstream reactivity. Implementation of two existing aldol technologies allows rapid access to all possible stereo-isomers of 1. The guiding principles during reaction optimization were reaction scalability and operational efficiency. Conversion of the amino acids to a variety of chiral building blocks in one to two steps demonstrates their synthetic utility. (C) 2011 Elsevier Ltd. All rights reserved.