methyl (4S,5S)-4-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyloxy)hexanoate | 914799-29-4

• 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 (4S,5S)-4-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyloxy)hexanoate
• 英文别名: methyl (4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 914799-29-4
• 化学式: C₁₈H₃₇NO₅Si
• 分子量: 375.581
• InChiKey: DTFAIJNYYRQJBT-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (4S,5S)-4-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyloxy)hexanoate 在 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 反应 24.5h， 生成 ((2S,3S)-6-Hydroxy-2-methyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl 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
• 作为产物：
  描述：

  Carbamic acid, [(1R,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-formylpropyl]-, 1,1-dimethylethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 26.0h， 生成 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

文献信息

• Synthetic Studies of<i>N</i>‐demethylossamine and Elaboration of its Glycosylation
  作者：Noriki Kutsumura、Shigeru Nishiyama

  DOI：10.1080/07328300600778793

  日期：2006.7

  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.