(1S,2S,3R,4R,5S)-2-O-(benzylcarbamoyl)-1-bromo-3,4-O-isopropylidene-5-methylcyclopentane-2,3,4-triol | 289698-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3R,4R,5S)-2-O-(benzylcarbamoyl)-1-bromo-3,4-O-isopropylidene-5-methylcyclopentane-2,3,4-triol
• 英文别名: (3aR,4S,5S,6S,6aR)-5-bromotetrahydro-2,2,6-trimethyl-4H-cyclopenta-1,3-dioxol-4-yl benzylcarbamate；[(3aR,4S,5S,6S,6aR)-5-bromo-2,2,6-trimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] N-benzylcarbamate
• CAS: 289698-47-1
• 化学式: C₁₇H₂₂BrNO₄
• 分子量: 384.27
• InChiKey: WGJWTOJTHILCOZ-COWZWYNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R,5S)-2-O-(benzylcarbamoyl)-1-bromo-3,4-O-isopropylidene-5-methylcyclopentane-2,3,4-triol 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 (1R,2R,3R,4R,5R)-4-amino-5-methylcyclopentane-1,2,3-triol hydrochloride
  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：

  (1S,2S,3R,4R)-2-O-(benzylcarbamoyl)-1-bromo-3,4-O-isopropylidene-5-methylidenecyclopentane-2,3,4-triol 在 Wilkinson's catalyst 氢气 作用下， 以 苯 为溶剂， 以74%的产率得到(1S,2S,3R,4R,5S)-2-O-(benzylcarbamoyl)-1-bromo-3,4-O-isopropylidene-5-methylcyclopentane-2,3,4-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：——