(4R)-苄基-4-脱氧-4-C-硝基甲基-B-D-阿拉伯糖苷 | 383173-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (4R)-苄基-4-脱氧-4-C-硝基甲基-B-D-阿拉伯糖苷
• 中文别名: (4R) - 苄基-4-脱氧-4-C-硝基甲基-B-D-阿拉伯糖苷
• 英文名称: Benzyl (4R)-4-deoxy-4-C-nitromethyl-β-D-arabino-pyranoside
• 英文别名: (4R)-Benzyl-4-deoxy-4-C-nitromethyl-b-D-arabinopyranoside；(2S,3S,4R,5R)-5-(nitromethyl)-2-phenylmethoxyoxane-3,4-diol
• CAS: 383173-71-5
• 化学式: C₁₃H₁₇NO₆
• 分子量: 283.281
• InChiKey: POWXZODMVVLAHO-FVCCEPFGSA-N

物化性质

• 熔点：
  104-106°C
• 沸点：
  488.8±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 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：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-苄基-4-脱氧-4-C-硝基甲基-B-D-阿拉伯糖苷 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 (2S,3S,4R,5R)-2-Benzyloxy-5-nonylaminomethyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Synthesis and Chemistry of Noeuromycin and Isofagomine Analogues

  摘要：

  Several N-substituted analogues of noeuromycin ((2RS,3S,4R,5R)-2,3,4-trihydroxy-5 -hydroxymethylpiperidine) and isofagomine ((3R,4R,5R)-3,4-dihydroxy-5-hydroxymethylpiperidine) were synthesised. The isofagomine analogues (3RS,4RS,5RS)N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxymethyl-piperidine, (3SR,4SR,5RS)-N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine, and (3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine were synthesised by direct alkylation of the corresponding azasugar. N-Substituted noeuromycin derivatives could not be made in this straightforward manner, but were made by modification of a synthesis intermediate. By this method (2RS,3S,4R,5R)-N-(4-methoxyphenyl)-2,3,4-trihydroxy-5-hydroxymethylpiperidine and (2RS,3S,4R,5R)-N-nonyl-2,3,4-trihydroxy-5-hydroxymethylpiperidine were synthesised. The stability of noeuromycin was studied and was found to depend on stereochemistry and pH. The L-fuco isomer ((2RS, 3R,4R,5R)-2,3,4-trihydroxy-5-methylpiperidine) was observed to undergo a particularly facile Amadori rearrangement at neutral pH to the 3-ketopiperidine. A noeuromycin analogue, that could not undergo the Amadori rearrangement, was synthesised.

  DOI：

  10.1081/car-200030070
• 作为产物：
  描述：

  Acetic acid (2R,3S,4S)-3,5-diacetoxy-2-benzyloxy-5-nitromethyl-tetrahydro-pyran-4-yl ester 在 sodium tetrahydroborate 、 甲醇 、 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 1.42h， 生成 (4R)-苄基-4-脱氧-4-C-硝基甲基-B-D-阿拉伯糖苷 、 Benzyl (4S)-4-deoxy-4-C-nitromethyl-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