(1R,2S,3R,4R,5R)-4-(benzylamino)-1,2-O-isopropylidene-5-methylcyclopentane-1,2,3-triol | 289698-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,3R,4R,5R)-4-(benzylamino)-1,2-O-isopropylidene-5-methylcyclopentane-1,2,3-triol
• 英文别名: (3aS,4R,5R,6R,6aR)-5-(benzylamino)tetrahydro-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-4-ol
• CAS: 289698-50-6
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: DCBISOOUNQGOLE-GZENYHORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  50.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4R,5R)-4-(benzylamino)-1,2-O-isopropylidene-5-methylcyclopentane-1,2,3-triol 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 (1R,2R,3R,4R,5R)-5-methyl-4-[(3-phenylpropyl)amino]cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Aminocyclopentitol Inhibitors ofα-L-Fucosidases

  摘要：

  Aminocyclopentitol analogs of alpha -L-fucose were synthesized stereoselectively from D-ribose. Alkyl substituents were attached at the NH2 group to mimic the glycosidic leaving group. The resulting (alkylamino)cyclopentitols inhibited alpha -L-fucosidases selectively with inhibition constants in the range of K-i = 10(-7) m. Comparisons with stereoisomers and acyclic analogs showed that this inhibition only occurs with N-alkyl substitution and proper configuration at the cyclopentane, as expected for transition-state-analog-type inhibition. These observations were supported by molecular-modeling comparisons between inhibitor and transition state.

  DOI：

  10.1002/1522-2675(20010711)84:7<2119::aid-hlca2119>3.0.co;2-8
• 作为产物：
  描述：

  (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 在 Wilkinson's catalyst sodium hydroxide 、 氢气 、 双氧水 、 sodium hydride 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 16.0h， 生成 (1R,2S,3R,4R,5R)-4-(benzylamino)-1,2-O-isopropylidene-5-methylcyclopentane-1,2,3-triol
  参考文献：
  名称：

  Aminocyclopentitol Inhibitors ofα-L-Fucosidases

  摘要：

  Aminocyclopentitol analogs of alpha -L-fucose were synthesized stereoselectively from D-ribose. Alkyl substituents were attached at the NH2 group to mimic the glycosidic leaving group. The resulting (alkylamino)cyclopentitols inhibited alpha -L-fucosidases selectively with inhibition constants in the range of K-i = 10(-7) m. Comparisons with stereoisomers and acyclic analogs showed that this inhibition only occurs with N-alkyl substitution and proper configuration at the cyclopentane, as expected for transition-state-analog-type inhibition. These observations were supported by molecular-modeling comparisons between inhibitor and transition state.

  DOI：

  10.1002/1522-2675(20010711)84:7<2119::aid-hlca2119>3.0.co;2-8

文献信息

• Blaser, Adrian; Reymond, Jean-Louis, Synlett, 2000, # 6, p. 817 - 819
  作者：Blaser, Adrian、Reymond, Jean-Louis

  DOI：——

  日期：——