Benzyl 2,3-di-O-acetyl-4-deoxy-4-C-nitromethylene-β-D-arabino-pyranoside

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Benzyl 2,3-di-O-acetyl-4-deoxy-4-C-nitromethylene-β-D-arabino-pyranoside
• 英文别名: Benzyl 2,3-DI-O-acetyl-4-deoxy-4-C-nitromethylene-beta-D-arabinopyranoside；[(2R,3S,4R,5E)-4-acetyloxy-5-(nitromethylidene)-2-phenylmethoxyoxan-3-yl] acetate
• 化学式: C₁₇H₁₉NO₈
• 分子量: 365.34
• InChiKey: AZEOAFROQDCKCF-KRYRETCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Benzyl 2,3-di-O-acetyl-4-deoxy-4-C-nitromethylene-β-D-arabino-pyranoside 在 10percent Pd/C 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以53%的产率得到(3R,4R,5R)-5-(羟基甲基)哌啶-3,4-二醇盐酸盐
  参考文献：
  名称：

  Efficient Synthesis of Isofagomine and Noeuromycin

  摘要：

  Starting from D-arabinose the synthesis of the very strong glycosidase inhibitors isofagomine (2) and noeuromycin (3) was achieved in six and seven steps, respectively. Keystep in the reaction sequence is the application of an efficient C-4 oxidation method to benzyl alpha -D-arabino-pyranoside. Subsequent Henry reaction of the obtained aldoketose with nitromethane provided the required branched carbohydrate precursors, which gave access to 2 and 3 in 17-21 % overall yield.

  DOI：

  10.1002/1521-3765(20010903)7:17<3744::aid-chem3744>3.0.co;2-3
• 作为产物：
  描述：

  苄基 2,3,4-三-O-乙酰基-4-硝基甲基-beta-D-阿拉伯吡喃糖 在 乙酸酐 、 silica gel 作用下， 以88%的产率得到Benzyl 2,3-di-O-acetyl-4-deoxy-4-C-nitromethylene-β-D-arabino-pyranoside
  参考文献：
  名称：

  Efficient Synthesis of Isofagomine and Noeuromycin

  摘要：

  Starting from D-arabinose the synthesis of the very strong glycosidase inhibitors isofagomine (2) and noeuromycin (3) was achieved in six and seven steps, respectively. Keystep in the reaction sequence is the application of an efficient C-4 oxidation method to benzyl alpha -D-arabino-pyranoside. Subsequent Henry reaction of the obtained aldoketose with nitromethane provided the required branched carbohydrate precursors, which gave access to 2 and 3 in 17-21 % overall yield.

  DOI：

  10.1002/1521-3765(20010903)7:17<3744::aid-chem3744>3.0.co;2-3

文献信息

• Efficient Synthesis of Isofagomine and Noeuromycin
  作者：Jens Andersch、Mikael Bols

  DOI：10.1002/1521-3765(20010903)7:17<3744::aid-chem3744>3.0.co;2-3

  日期：2001.9.3

  Starting from D-arabinose the synthesis of the very strong glycosidase inhibitors isofagomine (2) and noeuromycin (3) was achieved in six and seven steps, respectively. Keystep in the reaction sequence is the application of an efficient C-4 oxidation method to benzyl alpha -D-arabino-pyranoside. Subsequent Henry reaction of the obtained aldoketose with nitromethane provided the required branched carbohydrate precursors, which gave access to 2 and 3 in 17-21 % overall yield.