((1R,2R,3R,4R,5R)-2,3,4-Trihydroxy-5-methyl-cyclopentyl)-carbamic acid tert-butyl ester | 727404-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1R,2R,3R,4R,5R)-2,3,4-Trihydroxy-5-methyl-cyclopentyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R,2R,3R,4R,5R)-2,3,4-trihydroxy-5-methylcyclopentyl]carbamate
• CAS: 727404-60-6
• 化学式: C₁₁H₂₁NO₅
• 分子量: 247.291
• InChiKey: KUMKYINTFGKVBQ-JGKVKWKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((1R,2R,3R,4R,5R)-2,3,4-Trihydroxy-5-methyl-cyclopentyl)-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 水 为溶剂， 反应 5.5h， 以100%的产率得到(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：

  (1R,2S,3R,4R,5R)-4-(benzylamino)-1,2-O-isopropylidene-5-methylcyclopentane-1,2,3-triol 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 生成 ((1R,2R,3R,4R,5R)-2,3,4-Trihydroxy-5-methyl-cyclopentyl)-carbamic acid tert-butyl ester
  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