p-nitrophenyl 3-O-methyl-α-D-glucopyranoside | 150412-65-0

• 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-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-4-methoxy-6-(4-nitrophenoxy)oxane-3,5-diol
• CAS: 150412-65-0
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: HNKDHAGVHBOYLY-KVSVUVNWSA-N

物化性质

• 沸点：
  573.2±50.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

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-α-D-glucopyranoside 在 platinum(IV) oxide 氢气 、 sodium hydride 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.58h， 生成 4-((2S,3R,4S,5R,6R)-3,5-Bis-benzyloxy-4-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenylamine
  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
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetate-2-O-methyl-α-D-glucopyranoside 在 水 、 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 3.08h， 生成 p-nitrophenyl 3-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084

文献信息

• Synthesis of Monomethyl Derivatives of<i>P</i>-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases
  作者：Wataru Hakamata、Toshiyuki Nishio、Reiko Sato、Takahiro Mochizuki、Kazuya Tsuchiya、Maki Yasuda、Tadatake Oku

  DOI：10.1080/07328300008544084

  日期：2000.1

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.
• 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