p-nitrophenyl 3-O-methyl-β-D-glucopyranoside | 107150-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 3-O-methyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-4-methoxy-6-(4-nitrophenoxy)oxane-3,5-diol
• CAS: 107150-82-3
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: HNKDHAGVHBOYLY-NJMOYASZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 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：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 3-O-methyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 barium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 p-isothiocyanatophenyl 3-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of spacer-armed carbohydrate model compounds

  摘要：

  Commercially available chemicals, such as diethylene glycol, 1,9-nonanediol, 9-decen-1-ol, 1,2,6-hexanetriol, and p-nitrophenol were used to prepare spacer-armed carbohydrate derivatives. Glycosides of D-glucose, N-acetyl-D-glucosamine and 3-O-methyl-D-glucose have been synthesized, carrying reactive groups at the end of the spacer-arms. These glycosides are capable of forming neoglycoproteins. When bromo sugars were reacted with highly apolar aglycones in the presence of mercuric cyanide or mercuric bromide, a considerable amount of '2-OH-compounds' (such as 9-hydroxynonyl 3,4,6-tri-O-acetyl-beta-D-glucopyranoside) were formed. Some spacer-armed derivatives (such as 9,10-epoxydecyl beta-D-glucopyranoside) are theoretically a mixture of diastereomers, but this fact does not mirror in the H-1 and C-13 NMR spectra. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00256-x
• 作为产物：
  描述：

  p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85.2%的产率得到p-nitrophenyl 3-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  一种化学合成麻风分枝杆菌主要的具有血清学活性的糖脂的三糖以及末端二糖和单糖单元的新方法。

  摘要：

  合成对三氟乙酰氨基苯基O-（3,6-di-O-甲基-β-D-吡喃葡萄糖基）-（1-> 4）-O-（2,3-di-O-甲基的关键中间体-alp ha-L-鼠李糖吡喃糖基）-（1-> 2）-3-O-甲基-α-L-鼠李糖吡喃糖苷（15）以及对-三氟乙酰胺基苯基O-（3,6-di-O-甲基-β-D-吡喃葡萄糖基）-（1→4）-2,3-二-O-甲基-α-L-鼠李吡喃糖苷（29）是甲基和乙基O-（2-O-苄基-4 ，6-O-亚苄基-3-O-甲基-β-D-吡喃吡喃糖基）-（1-> 4）-2,3-O-二苯基亚甲基-1-硫代-α-L-鼠李糖吡喃糖苷（10和24） 。用10和24的二氯丙烷处理除去二苯基亚甲基，释放鼠李吡喃糖苷残基的HO-2和HO-3，并选择性地打开亚苄基乙缩醛，得到4-O-苄基-吡​​喃葡萄糖基二糖。游离OH基的甲基化产生了用作糖基供体的四-O-甲基1-硫代二糖（12和26）。这些临时保护基

  DOI：

  10.1016/0008-6215(93)80099-z

文献信息

• Jermyn, Australian Journal of Chemistry, 1957, vol. 10, p. 448,450
  作者：Jermyn

  DOI：——

  日期：——
• Camilleri, Patrick; Jones, Rosie F. D.; Kirby, Anthony J., Journal of the Chemical Society. Perkin transactions II, 1994, # 10, p. 2085 - 2090
  作者：Camilleri, Patrick、Jones, Rosie F. D.、Kirby, Anthony J.、Stroemberg, Roger

  DOI：——

  日期：——
• Syntheses of spacer-armed carbohydrate model compounds
  作者：János Kerékgyártó、Zoltán Nagy、Zoltán Szurmai

  DOI：10.1016/s0008-6215(96)00256-x

  日期：1997.1

  Commercially available chemicals, such as diethylene glycol, 1,9-nonanediol, 9-decen-1-ol, 1,2,6-hexanetriol, and p-nitrophenol were used to prepare spacer-armed carbohydrate derivatives. Glycosides of D-glucose, N-acetyl-D-glucosamine and 3-O-methyl-D-glucose have been synthesized, carrying reactive groups at the end of the spacer-arms. These glycosides are capable of forming neoglycoproteins. When bromo sugars were reacted with highly apolar aglycones in the presence of mercuric cyanide or mercuric bromide, a considerable amount of '2-OH-compounds' (such as 9-hydroxynonyl 3,4,6-tri-O-acetyl-beta-D-glucopyranoside) were formed. Some spacer-armed derivatives (such as 9,10-epoxydecyl beta-D-glucopyranoside) are theoretically a mixture of diastereomers, but this fact does not mirror in the H-1 and C-13 NMR spectra. (C) 1997 Elsevier Science Ltd.
• A new approach to the chemical synthesis of the trisaccharide, and the terminal di- and mono-saccharide units of the major, serologically active glycoplipid from Mycobacterium leprae
  作者：Anikó Borbás、András Lipták

  DOI：10.1016/0008-6215(93)80099-z

  日期：1993.3

  The key intermediates for the synthesis of p-trifluoroacetamidophenyl O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1-->4)-O-(2,3-di-O-methyl-alp ha-L- rhamnopyranosyl)-(1-->2)-3-O-methyl-alpha-L-rhamnopyranoside (15), as well as p-trifluoroacetamidophenyl O-(3,6-di-O-methyl-beta-D- glucopyranosyl)-(1-->4)-2,3-di-O-methyl-alpha-L-rhamnopyranoside (29), were the methyl and ethyl O-(2-O-benzyl-4,6-O-be

  合成对三氟乙酰氨基苯基O-（3,6-di-O-甲基-β-D-吡喃葡萄糖基）-（1-> 4）-O-（2,3-di-O-甲基的关键中间体-alp ha-L-鼠李糖吡喃糖基）-（1-> 2）-3-O-甲基-α-L-鼠李糖吡喃糖苷（15）以及对-三氟乙酰胺基苯基O-（3,6-di-O-甲基-β-D-吡喃葡萄糖基）-（1→4）-2,3-二-O-甲基-α-L-鼠李吡喃糖苷（29）是甲基和乙基O-（2-O-苄基-4 ，6-O-亚苄基-3-O-甲基-β-D-吡喃吡喃糖基）-（1-> 4）-2,3-O-二苯基亚甲基-1-硫代-α-L-鼠李糖吡喃糖苷（10和24） 。用10和24的二氯丙烷处理除去二苯基亚甲基，释放鼠李吡喃糖苷残基的HO-2和HO-3，并选择性地打开亚苄基乙缩醛，得到4-O-苄基-吡​​喃葡萄糖基二糖。游离OH基的甲基化产生了用作糖基供体的四-O-甲基1-硫代二糖（12和26）。这些临时保护基