苄基4-C-硝基甲基烯-beta-D-阿拉伯糖吡喃糖苷 | 383173-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苄基4-C-硝基甲基烯-beta-D-阿拉伯糖吡喃糖苷
• 中文别名: 苄基4-C-硝基亚甲基-β-D-阿拉伯吡喃糖苷；苄基4-C-硝基甲基-Β-D-阿拉伯吡喃糖苷
• 英文名称: Benzyl 4-C-nitromethyl-β-D-arabino-pyranoside
• 英文别名: Benzyl 4-C-Nitromethylene-|A-D-arabinopyranoside；(2R,3S,4S,5R)-5-(nitromethyl)-2-phenylmethoxyoxane-3,4,5-triol
• CAS: 383173-64-6
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: MCEJVWPYHIIEJJ-WUHRBBMRSA-N

物化性质

• 熔点：
  189-191?C
• 沸点：
  513.8±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)
• 溶解度：
  溶于丙酮

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苄基4-C-硝基甲基烯-beta-D-阿拉伯糖吡喃糖苷 在 10percent Pd/C 氢气 、 乙酸酐 、 silica gel 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (3R,4R,5S)-5-(羟基甲基)-3,4-哌啶二醇
  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：

  (-)-benzyl β-D-arabinopyranoside 在 3 A molecular sieve 、 三乙胺 、 三丁基氧化锡 作用下， 以 氯仿 为溶剂， 反应 4.55h， 生成 苄基4-C-硝基甲基烯-beta-D-阿拉伯糖吡喃糖苷
  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.