methyl 3-nitro-β-D-3-deoxy-glucopyranoside | 4631-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-nitro-β-D-3-deoxy-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-methoxy-4-nitrooxane-3,5-diol
• CAS: 4631-21-4
• 化学式: C₇H₁₃NO₇
• 分子量: 223.183
• InChiKey: PQPUXJMPHURQIH-IECVIRLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  methyl 3-nitro-β-D-3-deoxy-glucopyranoside 在 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以84%的产率得到methyl-β-kanopyranosaminide
  参考文献：
  名称：

  A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol

  摘要：

  3-Acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.016
• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 sodium periodate 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 25.0h， 生成 methyl 3-nitro-β-D-3-deoxy-glucopyranoside
  参考文献：
  名称：

  Carbohydrate-Based Small-Molecule Scaffolds for the Construction of Universal Pharmacophore Mapping Libraries

  摘要：

  DOI：

  10.1021/jo980164m

文献信息

• Reactions of nitro sugars. XVII. Koenigs–Knorr syntheses
  作者：Hans H. Baer、Werner Rank、Frank Kienzle

  DOI：10.1139/v70-214

  日期：1970.4.15

  Starting from methyl 3-deoxy-3-nitro-β-D-glucopyranoside (1), the free sugar 3-deoxy-3-nitro-α-D-glucopyranose (2), its tetraacetate (3), and 2,4,6-tri-O-acetyl-3-deoxy-3-nitro-α-D-glucopyranosyl bromide (4) were prepared. Another sequence of reactions commencing with 1 gave the 6-O-trityl (6), the 2,4-di-O-acetyl-6-O-trityl (7), the 2,4,6-tri-O-acetyl (8), and the 2,6-di-O-acetyl (10) derivatives of 1, whereas the 2,4-di-O-acetyl derivative (9) could not be isolated in pure form because of acetyl group migration. Reaction of the bromide 4 with water, methanol, and benzyl alcohol, respectively, led to 2,4,6-tri-O-acetyl-3-deoxy-3-nitro-β-D-glucopyranose (5) and the corresponding methyl and benzyl β-D-glycosides (8 and 11). Condensation of 4 with 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose (12), and condensation of tetra-O-acetyl-α-D-glucopyranosyl bromide (14) with the trityl compound 6, furnished derivatives of gentiobiose having a deoxynitro function at C-3′ (13) and C-3 (15), respectively.

  从甲基3-去氧-3-硝基-β-D-葡萄糖吡喃苷（1）开始，制备了自由糖3-去氧-3-硝基-α-D-葡萄糖吡喃糖（2）、其四乙酰基（3）、以及2,4,6-三-O-乙酰基-3-去氧-3-硝基-α-D-葡萄糖吡喃基溴化物（4）。另一个以1为起点的反应序列得到了6-O-三苄基（6）、2,4-二-O-乙酰基-6-O-三苄基（7）、2,4,6-三-O-乙酰基（8）和2,6-二-O-乙酰基（10）衍生物，而2,4-二-O-乙酰基衍生物（9）由于乙酰基迁移无法纯化。将溴化物4分别与水、甲醇和苄醇反应，得到2,4,6-三-O-乙酰基-3-去氧-3-硝基-β-D-葡萄糖吡喃糖（5）以及相应的甲基和苄基β-D-糖苷（8和11）。将4与1,2,3,4-四-O-乙酰基-β-D-葡萄糖吡喃糖（12）以及四-O-乙酰基-α-D-葡萄糖吡喃基溴化物（14）与三苄基化合物6进行缩合反应，分别得到在C-3'（13）和C-3（15）位置具有去氧硝基功能的龙胆二糖衍生物。
• Carbohydrate-Based Small-Molecule Scaffolds for the Construction of Universal Pharmacophore Mapping Libraries
  作者：Michael J. Sofia、Rachael Hunter、Tin Yau Chan、Andrew Vaughan、Richard Dulina、Huiming Wang、David Gange

  DOI：10.1021/jo980164m

  日期：1998.5.1
• A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol
  作者：Ondřej Šimák、Jan Staněk、Jitka Moravcová

  DOI：10.1016/j.carres.2009.03.016

  日期：2009.5

  3-Acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale. (C) 2009 Elsevier Ltd. All rights reserved.