(2R,3R,4R,6S)-3,4-di(benzyloxy)-2-benzyloxymethyl-1-azabicyclo[4.1.0]heptane | 605675-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R,6S)-3,4-di(benzyloxy)-2-benzyloxymethyl-1-azabicyclo[4.1.0]heptane
• 英文别名: (2R,3R,4R,6S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-1-azabicyclo[4.1.0]heptane
• CAS: 605675-52-3
• 化学式: C₂₈H₃₁NO₃
• 分子量: 429.559
• InChiKey: GLOZKRQZQAQXMH-KBVNRVAUSA-N

物化性质

• 沸点：
  542.1±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,6S)-3,4-di(benzyloxy)-2-benzyloxymethyl-1-azabicyclo[4.1.0]heptane 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 2,3,6-trideoxy-2,6-imino-D-manno-heptitol
  参考文献：
  名称：

  General synthesis and biological evaluation of α-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-α-C-glycosides)

  摘要：

  A general synthesis of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is described. The nine-step reaction sequence proceeded in an overall yield of 14-28% from tri-O-benzyl-D-glucal. Biological evaluation of alpha-1-C-substituted derivatives of fagomine, of the 2-deoxy analog of alpha-homonojirimycin 19 and its 1,N-anhydro derivative 22 as glycosidase inhibitors is reported. The glycosyl phosphate mimetic 15k was found to display no inhibitory activity towards glycogen phosphorylase b and phosphoglucomutase. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.043
• 作为产物：
  描述：

  3,4,6-三-氧-苄基-2-脱氧-D-吡喃葡萄糖 在 N-碘代丁二酰亚胺 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 sodium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 乙二胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 35.0h， 生成 (2R,3R,4R,6S)-3,4-di(benzyloxy)-2-benzyloxymethyl-1-azabicyclo[4.1.0]heptane
  参考文献：
  名称：

  General synthesis and biological evaluation of α-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-α-C-glycosides)

  摘要：

  A general synthesis of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is described. The nine-step reaction sequence proceeded in an overall yield of 14-28% from tri-O-benzyl-D-glucal. Biological evaluation of alpha-1-C-substituted derivatives of fagomine, of the 2-deoxy analog of alpha-homonojirimycin 19 and its 1,N-anhydro derivative 22 as glycosidase inhibitors is reported. The glycosyl phosphate mimetic 15k was found to display no inhibitory activity towards glycogen phosphorylase b and phosphoglucomutase. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.043