4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside | 570412-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside
• 英文别名: (2R,3S,4R,5S,6S)-5-azido-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4-diol
• CAS: 570412-05-4
• 化学式: C₁₂H₁₄N₄O₇
• 分子量: 326.266
• InChiKey: KTWQZFHYGZLIJI-IYKVGLELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside 在 吡啶 、 甲醇 、 sodium methylate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-nitrophenyl 2-acetamido-2-deoxy-β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-β-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-α-D-mannopyranoside

  摘要：

  这些标题化合物是通过选择性还原4-硝基苯基3,4,6-三O-乙酰基-2-叠氮-2-脱氧-α-D-甘露聚糖 (8) 和 4-硝基苯基3,4,6-三O-乙酰基-2-叠氮-2-脱氧-β-D-甘露聚糖 (11) 中的叠氮基，并随后进行乙酰化合成的。 化合物8是通过用硝基苯酚对甲基2,3-环氧-4,6-O-苄基亚甲基-α-D-葡萄糖聚糖 (1) 进行环氧环开启，然后在产生的阿尔托吡喃糖中C-3处的构型倒置，最后与4-硝基苯酚进行糖苷化而制备的。

  DOI：

  10.1135/cccc20030801
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl glucopyranose 在 sodium azide 、 氢溴酸 、 sodium methylate 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 37.33h， 生成 4-nitrophenyl 2-azido-2-deoxy-β-D-mannopyranoside
  参考文献：
  名称：

  A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-d-mannopyranosides

  摘要：

  4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha- and beta1-D-mannopyranosides were prepared from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D- and -beta-D-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-mannopyranoside in 20 % and 44 % overall yields, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.002

文献信息

• Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-β-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-α-D-mannopyranoside
  作者：Pavel Krist、Marek Kuzma、István F. Pelyvás、Pavla Simerská、Vladimír Křen

  DOI：10.1135/cccc20030801

  日期：——

  The title compounds were synthesized by the selective reduction of the azido group in 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (8) and 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-mannopyranoside (11), and by subsequent acetylation. Compound8was prepared by opening of the epoxide ring in methyl 2,3-anhydro-4,6-O-benzylidene-α-D-glucopyranoside (1) with sodium azide, followed by inversion of the configuration at C-3 in the resulting altropyranoside and glycosidation with 4-nitrophenol.

  这些标题化合物是通过选择性还原4-硝基苯基3,4,6-三O-乙酰基-2-叠氮-2-脱氧-α-D-甘露聚糖 (8) 和 4-硝基苯基3,4,6-三O-乙酰基-2-叠氮-2-脱氧-β-D-甘露聚糖 (11) 中的叠氮基，并随后进行乙酰化合成的。 化合物8是通过用硝基苯酚对甲基2,3-环氧-4,6-O-苄基亚甲基-α-D-葡萄糖聚糖 (1) 进行环氧环开启，然后在产生的阿尔托吡喃糖中C-3处的构型倒置，最后与4-硝基苯酚进行糖苷化而制备的。
• A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-d-mannopyranosides
  作者：Alena Popelová、Karel Kefurt、Martina Hlaváčková、Jitka Moravcová

  DOI：10.1016/j.carres.2004.11.002

  日期：2005.1

  4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha- and beta1-D-mannopyranosides were prepared from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D- and -beta-D-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-mannopyranoside in 20 % and 44 % overall yields, respectively. (C) 2004 Elsevier Ltd. All rights reserved.