4-nitrophenyl 2-acetamido-2-deoxy-β-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 2-acetamido-2-deoxy-β-D-mannopyranoside
• 英文别名: N-[(2S,3S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• 化学式: C₁₄H₁₈N₂O₈
• 分子量: 342.306
• InChiKey: OMRLTNCLYHKQCK-XVIXHAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 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：
  154
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-nitrophenyl 3,4,6-tri-O-acetyl-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

文献信息

• Syntheses of p-nitrophenyl 3- and 4-thio-β-d-glycopyranosides
  作者：Hong-Ming Chen、Stephen G. Withers

  DOI：10.1016/j.carres.2010.10.001

  日期：2010.12

  Thioglycosides have proved to be useful, enzymatically stable analogs of glycosides for structural and mechanistic studies and their synthesis is considerably simplified through the use of thioglycoligases. As part of an investigation into the use of thioglycosides as potential pharmacological chaperones, and as components of glycoproteins and glycolipids, the syntheses of p-nitrophenyl 3-thio-β-D-galactopyranoside

  硫代糖苷已被证明是有用的，酶学稳定的糖苷类似物，用于结构和机理研究，并且通过使用硫代糖醇大大简化了它们的合成。作为使用硫代糖苷作为潜在药理伴侣以及作为糖蛋白和糖脂成分的研究的一部分，对硝基苯基3-硫代-β-D-吡喃半乳糖苷，苯基1,4-二硫代-β-D-描述了吡喃葡萄糖苷，对硝基苯基4-硫代-β-D-甘露吡喃糖苷和对硝基苯基2-乙酰氨基-2-脱氧-4-硫代-β-D-甘露吡喃糖苷。
• 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.
• 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。