tert-butyl (2R,3S)-2-(tert-butyldimethylsilyl)oxy-3-methyl-4-(methylamino)(4-oxobutyl)(methyl)carbamate | 1326727-03-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (2R,3S)-2-(tert-butyldimethylsilyl)oxy-3-methyl-4-(methylamino)(4-oxobutyl)(methyl)carbamate
• 英文别名: tert-butyl ((2R,3S)-2-((tert-butyldimethylsilyl)oxy)-3-methyl-4-(methylamino)-4-oxobutyl)(methyl)carbamate
• CAS: 1326727-03-0
• 化学式: C₁₈H₃₈N₂O₄Si
• 分子量: 374.596
• InChiKey: GVKKAYPMCAVSOR-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3S)-2-(tert-butyldimethylsilyl)oxy-3-methyl-4-(methylamino)(4-oxobutyl)(methyl)carbamate 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以84%的产率得到tert-butyl (2R,3R)-2-(tert-butyldimethylsilyl)oxy-3-methyl-4-(methylamino)butyl(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
• 作为产物：
  描述：

  在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 tert-butyl (2R,3S)-2-(tert-butyldimethylsilyl)oxy-3-methyl-4-(methylamino)(4-oxobutyl)(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