N-[(1R,2S,3S,4R,5S)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclopentyl]acetamide | 257602-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(1R,2S,3S,4R,5S)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclopentyl]acetamide
• CAS: 257602-67-8
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: YIKVZIMPNYXBMM-YQXRAVKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(1R,2S,3S,4R,5S)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclopentyl]acetamide 在 盐酸 作用下， 反应 15.0h， 以100%的产率得到(1R,2S,3S,4R,5S)-4-Amino-5-hydroxymethyl-cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Synthesis and Evaluation of Aminocyclopentitol Inhibitors of β-Glucosidases

  摘要：

  [GRAPHICS](1R,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1, prepared from D-glucose, inhibits beta-glucosidases from Caldocellum saccharolyticum (K-i = 1.8 x 10(-7) M) and from almonds (K-i = 3.4 x 10(-6) M). Inhibition is not influenced by N-ethylation (--> 15) but is strongly reduced upon N-acetylation (--> 12). Inversion of stereochemistry at C(5) (--> 14) has little effect on inhibition of beta-glucosidases. These experiments suggest that 1 acts as an analogue of a protonated beta-glucoside.

  DOI：

  10.1021/ol991252b
• 作为产物：
  描述：

  O-benzyl-N-[(1R,2S,3S,4R,5S)-2,3,4-tris-benzyloxy-5-benzyloxymethylcyclopentyl]-N-hydroxylamine 在 palladium on activated charcoal 氢气 、 锌 作用下， 以 乙醇 为溶剂， 25.0~135.0 ℃ 、1.01 MPa 条件下， 反应 244.0h， 生成 N-[(1R,2S,3S,4R,5S)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclopentyl]acetamide
  参考文献：
  名称：

  Synthesis and Evaluation of Aminocyclopentitol Inhibitors of β-Glucosidases

  摘要：

  [GRAPHICS](1R,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1, prepared from D-glucose, inhibits beta-glucosidases from Caldocellum saccharolyticum (K-i = 1.8 x 10(-7) M) and from almonds (K-i = 3.4 x 10(-6) M). Inhibition is not influenced by N-ethylation (--> 15) but is strongly reduced upon N-acetylation (--> 12). Inversion of stereochemistry at C(5) (--> 14) has little effect on inhibition of beta-glucosidases. These experiments suggest that 1 acts as an analogue of a protonated beta-glucoside.

  DOI：

  10.1021/ol991252b