p-methoxyphenyl β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 211423-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(β-D-glucopyranosyl)-β-D-glucopyranoside；2-[(2S,3R,4R,5S,6R)-2-(4-methoxyphenoxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]isoindole-1,3-dione
• CAS: 211423-02-8
• 化学式: C₄₁H₄₃NO₁₃
• 分子量: 757.791
• InChiKey: IRAYYZCQEYXTGK-LAEKHFNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  183
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 palladium hydroxide - carbon 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 3.0h， 生成
  参考文献：
  名称：

  Introduction ofC-Sulfonate Groups into Disaccharide Derivatives

  摘要：

  To prepare C-sulfonate derivatives of disaccharides two different strategies were followed. Thus 6- and 6'-C-sulfocellobiosides 4 and 10-12 were prepared starting from a suitably protected cellobioside. The 6'-C-sulfoaminocellobioside 18 was prepared by construction of the molecule through a glycosylation reaction. In both cases, the synthetic pathway involves regioselective tosylation, introduction of a sulfur atom by nucleophilic displacement with potassium thioacetate and oxidation with hydrogen peroxide.

  DOI：

  10.1080/00397919808004290
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 p-methoxyphenyl β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Introduction ofC-Sulfonate Groups into Disaccharide Derivatives

  摘要：

  To prepare C-sulfonate derivatives of disaccharides two different strategies were followed. Thus 6- and 6'-C-sulfocellobiosides 4 and 10-12 were prepared starting from a suitably protected cellobioside. The 6'-C-sulfoaminocellobioside 18 was prepared by construction of the molecule through a glycosylation reaction. In both cases, the synthetic pathway involves regioselective tosylation, introduction of a sulfur atom by nucleophilic displacement with potassium thioacetate and oxidation with hydrogen peroxide.

  DOI：

  10.1080/00397919808004290

文献信息

• Synthesis and biological evaluation of oligosaccharides related to the molecule signals in plant defence and the Rhizobium-legume symbiosis
  作者：I Robina、S Gómez-Bujedo、J.G Fernández-Bolaños、J Fuentes、H.P Spaink

  DOI：10.1016/s0040-4020(01)01148-6

  日期：2002.1

  The synthesis of tetrasaccharides related to the chitinoligosaccharides involved in plant defence and Rhizobium-legume symbiosis is reported. One and two central GlcNAc residues of the chitin backbone have been replaced by Glc units. A biological evaluation using Catharanthus roseaus assay indicates that the replacement of the two central units produces a total loss of activity. However, the replacement of the GlcNAc moiety close to the reducing end by Glc in the chitin tetramer, does not reduce its activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Introduction of<i>C</i>-Sulfonate Groups into Disaccharide Derivatives
  作者：Inmaculada Robina、Silvia Gómez-Bujedo、José G. Fernández-Bolaños、José Fuentes

  DOI：10.1080/00397919808004290

  日期：1998.7

  To prepare C-sulfonate derivatives of disaccharides two different strategies were followed. Thus 6- and 6'-C-sulfocellobiosides 4 and 10-12 were prepared starting from a suitably protected cellobioside. The 6'-C-sulfoaminocellobioside 18 was prepared by construction of the molecule through a glycosylation reaction. In both cases, the synthetic pathway involves regioselective tosylation, introduction of a sulfur atom by nucleophilic displacement with potassium thioacetate and oxidation with hydrogen peroxide.