(1R,2R,3R,4S,5R)-4-氨基-5-甲基-1,2,3-环戊烷三醇 | 229962-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2R,3R,4S,5R)-4-氨基-5-甲基-1,2,3-环戊烷三醇
• 中文别名: 3-[3-(4-硝基苯基)三氮烯基-1-基]丁烷-2-酮
• 英文名称: (1R,2R,3R,4S,5R)-4-amino-5-methylcyclopentane-1,2,3-triol
• 英文别名: 1,2,3-Cyclopentanetriol,4-amino-5-methyl-,(1R,2R,3R,4S,5R)-(9CI)
• CAS: 229962-59-8
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: PTEOOBZJCIANPX-AIECOIEWSA-N

物化性质

• 沸点：
  254.8±40.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (1R,2R,3R,4S,5R)-4-氨基-5-甲基-1,2,3-环戊烷三醇 在 titanium(IV) isopropylate 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 以27%的产率得到(1R,2R,3R,4S,5R)-4-(benzylamino)-5-methylcyclopentane-1,2,3-triol
  参考文献：
  名称：

  Stereoselective Inhibition of α-l-Fucosidases by N-Benzyl Aminocyclopentitols

  摘要：

  [GRAPHICS](1R,2R,3R,4R,5R)-4-Amino-5-methylcyclopentane-1,2,3-triol 8, its 4S stereoisomer 9, and their acyclic analogues (R)- and (S)-5-aminobutanol 11 and 12 are selective but moderate inhibitors of alpha-L-fucosidases. N-Benzylation selectively enhances inhibition potency for aminocyclopentitol 8 ( --> 1, K-i = 6.8 x 10(-7) M) but decreases inhibition for its 4S-stereoisomer 9 (--> 2, K-i = 1.1 x 10(-4) M) and for the aminobutanols 11 ( --> 13, no inhibition) and 12 ( --> 14, no inhibition).

  DOI：

  10.1021/ol005895z
• 作为产物：
  描述：

  (1aS,1bR,4aR,5aR)-tetrahydro-3,3-dimethyl-5-methylidene-5H-oxireno[3,4]cyclopenta[1,2-d][1,3]dioxol 在 palladium on activated charcoal 盐酸 、 氨 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (1R,2R,3R,4S,5R)-4-氨基-5-甲基-1,2,3-环戊烷三醇
  参考文献：
  名称：

  A Selectiveα-L-Fucosidase Inhibitor Based on an Aminocyclopentane Framework

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<760::aid-hlca760>3.0.co;2-s

文献信息

• Aminocyclopentitol Inhibitors ofα-L-Fucosidases
  作者：Adrian Blaser、Jean-Louis Reymond

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

  日期：2001.7.11

  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.