N-benzhydryl-1,5-dideoxy-1,5-imino-D-galactitol | 188778-97-4

• 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: N-benzhydryl-1,5-dideoxy-1,5-imino-D-galactitol
• 英文别名: (2R,3S,4R,5S)-1-benzhydryl-2-(hydroxymethyl)piperidine-3,4,5-triol
• CAS: 188778-97-4
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: KIEOHSDEGULDGN-KCITZHQASA-N

物化性质

• 沸点：
  554.0±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzhydryl-1,5-dideoxy-1,5-imino-D-galactitol 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 米加司他
  参考文献：
  名称：

  Double reductive amination of l-arabino-hexos-5-uloses: A diastereoselective approach to 1-deoxy-d-galactostatin derivatives

  摘要：

  The double reductive amination of L-arabino-hexos-5-ulose with benzhydrylamine and NaBH3CN takes place in a diastereospecific manner giving in moderate chemical yield (36%) the galactosidase inhibitor 1-deoxy-D-galactostatin. The aminocyclization of 2,6-di-O-benzyl-L-arabino-hexos-5-ulose is more complicated giving results dependent from the type of amine: with ammonia or methylamine a mixture of C-5 epimeric 1-deoxyazapyranoses (D-galacto/L-altro ratio approximate to 4:1) is obtained in 45-65% combined yield, while with benzhydrylamine substantial amounts of an acyclic 1-deoxyl-benzydrylamino-hexitol (10% yield) is isolated together with the expected 1-deoxy-azasugars of the D-galacto and L-altro series. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00063-x
• 作为产物：
  描述：

  L-arabino-hexos-5-ulose 、 二苯甲胺 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以36%的产率得到N-benzhydryl-1,5-dideoxy-1,5-imino-D-galactitol
  参考文献：
  名称：

  Double reductive amination of l-arabino-hexos-5-uloses: A diastereoselective approach to 1-deoxy-d-galactostatin derivatives

  摘要：

  The double reductive amination of L-arabino-hexos-5-ulose with benzhydrylamine and NaBH3CN takes place in a diastereospecific manner giving in moderate chemical yield (36%) the galactosidase inhibitor 1-deoxy-D-galactostatin. The aminocyclization of 2,6-di-O-benzyl-L-arabino-hexos-5-ulose is more complicated giving results dependent from the type of amine: with ammonia or methylamine a mixture of C-5 epimeric 1-deoxyazapyranoses (D-galacto/L-altro ratio approximate to 4:1) is obtained in 45-65% combined yield, while with benzhydrylamine substantial amounts of an acyclic 1-deoxyl-benzydrylamino-hexitol (10% yield) is isolated together with the expected 1-deoxy-azasugars of the D-galacto and L-altro series. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00063-x

文献信息

• Double reductive amination of l-arabino-hexos-5-uloses: A diastereoselective approach to 1-deoxy-d-galactostatin derivatives
  作者：Pier Luigi Barili、Giancarlo Berti、Giorgio Catelani、Felicia D'andrea、Francesco De Rensis、Leonardo Puccioni

  DOI：10.1016/s0040-4020(97)00063-x

  日期：1997.3

  The double reductive amination of L-arabino-hexos-5-ulose with benzhydrylamine and NaBH3CN takes place in a diastereospecific manner giving in moderate chemical yield (36%) the galactosidase inhibitor 1-deoxy-D-galactostatin. The aminocyclization of 2,6-di-O-benzyl-L-arabino-hexos-5-ulose is more complicated giving results dependent from the type of amine: with ammonia or methylamine a mixture of C-5 epimeric 1-deoxyazapyranoses (D-galacto/L-altro ratio approximate to 4:1) is obtained in 45-65% combined yield, while with benzhydrylamine substantial amounts of an acyclic 1-deoxyl-benzydrylamino-hexitol (10% yield) is isolated together with the expected 1-deoxy-azasugars of the D-galacto and L-altro series. (C) 1997 Elsevier Science Ltd.