(E)-(4S,5S)-4-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester | 914799-35-2

• 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: (E)-(4S,5S)-4-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester
• CAS: 914799-35-2
• 化学式: C₁₈H₃₅NO₅Si
• 分子量: 373.565
• InChiKey: SCDWJGKIJUSQLA-GHYUOPHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 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：
  0.78
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-(4S,5S)-4-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以97%的产率得到methyl (4S,5S)-4-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyloxy)hexanoate
  参考文献：
  名称：

  Synthetic Studies ofN‐demethylossamine and Elaboration of its Glycosylation

  摘要：

  An amino-sugar, N -demethylossamine, was efficiently synthesized from D-threonine, two stereogenic centers of which were directly used as those at the C-4 and 5 positions of the target sugar. In addition, the glycosylation study indicated that reaction of the acetate 7 with cyclopentanol under Lewis acid conditions, provided the desired alpha-L-glycoside 9 alpha.

  DOI：

  10.1080/07328300600778793
• 作为产物：
  描述：

  [(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-propyl]-carbamic acid tert-butyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 (E)-(4S,5S)-4-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthetic Studies ofN‐demethylossamine and Elaboration of its Glycosylation

  摘要：

  An amino-sugar, N -demethylossamine, was efficiently synthesized from D-threonine, two stereogenic centers of which were directly used as those at the C-4 and 5 positions of the target sugar. In addition, the glycosylation study indicated that reaction of the acetate 7 with cyclopentanol under Lewis acid conditions, provided the desired alpha-L-glycoside 9 alpha.

  DOI：

  10.1080/07328300600778793