(2R,3S)-4-tert-butyldimethylsilyloxy-N-methoxycarbonyl-3-methoxymethyloxy-2-butylamine | 175730-22-0

• 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: (2R,3S)-4-tert-butyldimethylsilyloxy-N-methoxycarbonyl-3-methoxymethyloxy-2-butylamine
• 英文别名: methyl N-[(2R,3S)-4-[tert-butyl(dimethyl)silyl]oxy-3-(methoxymethoxy)butan-2-yl]carbamate
• CAS: 175730-22-0
• 化学式: C₁₄H₃₁NO₅Si
• 分子量: 321.489
• InChiKey: DUTPSFVFOCUVGG-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-4-tert-butyldimethylsilyloxy-N-methoxycarbonyl-3-methoxymethyloxy-2-butylamine 在 sodium dichromate 、 草酰氯 、 硫酸 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.17h， 生成 (2S,3R)-3-methoxycarbonylamino-2-methoxymethyloxybutanoic acid
  参考文献：
  名称：

  Stereoselective synthesis of α-hydroxy-β-amino acids using D-glyceraldehyde as the homochiral source

  摘要：

  A systematic study of the diastereoselective addition of methyl organometallic compounds to the benzyl imine derived from conveniently protected D-glyceraldehyde in order to develop a new approach to enantiomerically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesium bromide addition afforded the corresponding adduct, which can be further elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.

  DOI：

  10.1016/0957-4166(96)00037-7
• 作为产物：
  描述：

  (2R,3S)-N-benzyl-3,4-dibenzyloxy-N-methoxycarbonyl-2-butylamine 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 (2R,3S)-4-tert-butyldimethylsilyloxy-N-methoxycarbonyl-3-methoxymethyloxy-2-butylamine
  参考文献：
  名称：

  Stereoselective synthesis of α-hydroxy-β-amino acids using D-glyceraldehyde as the homochiral source

  摘要：

  A systematic study of the diastereoselective addition of methyl organometallic compounds to the benzyl imine derived from conveniently protected D-glyceraldehyde in order to develop a new approach to enantiomerically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesium bromide addition afforded the corresponding adduct, which can be further elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.

  DOI：

  10.1016/0957-4166(96)00037-7

文献信息

• Stereoselective synthesis of α-hydroxy-β-amino acids using D-glyceraldehyde as the homochiral source
  作者：Carlos Cativiela、Maria D. Diaz-de-Villegas、JoséA. Gálvez

  DOI：10.1016/0957-4166(96)00037-7

  日期：1996.2

  A systematic study of the diastereoselective addition of methyl organometallic compounds to the benzyl imine derived from conveniently protected D-glyceraldehyde in order to develop a new approach to enantiomerically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesium bromide addition afforded the corresponding adduct, which can be further elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.