methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethoxy-2-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]butanoate | 566198-51-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethoxy-2-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]butanoate
• CAS: 566198-51-4
• 化学式: C₂₉H₄₂N₂O₉Si
• 分子量: 590.746
• InChiKey: FOBWGCVEKQVEIJ-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethoxy-2-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]butanoate 在 palladium on activated charcoal 氢气 、 镍 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 19.5h， 生成 (2S,3R)-methyl 2-amino-3-t-butyldimethylsilyloxy-4,4-dimethoxybutanoate
  参考文献：
  名称：

  Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins

  摘要：

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00460-x
• 作为产物：
  描述：

  4,4-二甲氧基乙酰乙酸甲酯 在 2,6-二甲基吡啶 、 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 、 氢气 、 三乙胺 、 zinc methyl bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~65.0 ℃ 、101.33 kPa 条件下， 反应 18.5h， 生成 methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethoxy-2-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]butanoate
  参考文献：
  名称：

  Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins

  摘要：

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00460-x

文献信息

• Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins
  作者：Bruno Drouillat、Olivia Poupardin、Yann Bourdreux、Christine Greck

  DOI：10.1016/s0040-4039(03)00460-x

  日期：2003.3

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.