4,5,7-tri-O-benzyl-1-O-butanoyl-N-butyl-2,3,6-trideoxy-2,6-imino-D-manno-heptitol | 850190-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4,5,7-tri-O-benzyl-1-O-butanoyl-N-butyl-2,3,6-trideoxy-2,6-imino-D-manno-heptitol
• CAS: 850190-34-0
• 化学式: C₃₆H₄₇NO₅
• 分子量: 573.773
• InChiKey: PFOVIRYJXOGNQM-VBKJKXFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  42.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,5,7-tri-O-benzyl-1-O-butanoyl-N-butyl-2,3,6-trideoxy-2,6-imino-D-manno-heptitol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以88%的产率得到N-butyl-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：

  4,5,7-tri-O-benzyl-1,2,3-trideoxy-L-xylo-hept-1-enitol 在 N-碘代丁二酰亚胺 、 偶氮二甲酸二异丙酯 、 4 A molecular sieve 、 sodium cyanoborohydride 、 溶剂黄146 、 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 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 4,5,7-tri-O-benzyl-1-O-butanoyl-N-butyl-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