(3aR,3bR,6aR,7R,7aR)-6-benzylhexahydro-2,2,7-trimethyl-5H-1,3-dioxolo[4,5:3,4]cyclopent[1,2-d]oxazol-5-one | 286851-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,3bR,6aR,7R,7aR)-6-benzylhexahydro-2,2,7-trimethyl-5H-1,3-dioxolo[4,5:3,4]cyclopent[1,2-d]oxazol-5-one
• 英文别名: (1R,2R,6R,7R,8R)-9-benzyl-4,4,7-trimethyl-3,5,11-trioxa-9-azatricyclo[6.3.0.02,6]undecan-10-one
• CAS: 286851-33-0
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: GUDXCFITUTYOAH-DIAXPKBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,3bR,6aR,7R,7aR)-6-benzylhexahydro-2,2,7-trimethyl-5H-1,3-dioxolo[4,5:3,4]cyclopent[1,2-d]oxazol-5-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以91%的产率得到(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
• 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 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 12.5h， 生成 (3aR,3bR,6aR,7R,7aR)-6-benzylhexahydro-2,2,7-trimethyl-5H-1,3-dioxolo[4,5:3,4]cyclopent[1,2-d]oxazol-5-one
  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：——
• Stereoselective Inhibition of α-<scp>l</scp>-Fucosidases by <i>N</i>-Benzyl Aminocyclopentitols
  作者：Adrian Blaser、Jean-Louis Reymond

  DOI：10.1021/ol005895z

  日期：2000.6.1

  [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).