methyl(2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 200712-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl(2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: [(4aS,6S,7R,8S,8aR)-8-methoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 200712-56-7
• 化学式: C₄₅H₅₂O₁₂
• 分子量: 784.901
• InChiKey: VNKUFDWNXJSZFY-KOKVLQSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl(2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 chromium(VI) oxide 、 4-二甲氨基吡啶 、 硫酸 、 水 、 sodium methylate 、 sodium hydride 、 potassium hydrogencarbonate 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 13.42h， 生成 (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-1,3,6-tri-O-acetyl-2-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  Identification of a hexasaccharide sequence able to inhibit thrombin and suitable for ‘polymerisation’

  摘要：

  Three hexasaccharides, having from low to very high affinity for antithrombin, were synthesised from disaccharide building block precursors. One of them, methyl(sodium 2,3-di-O-methyl-4-O-sodium sulfonato-alpha-L-idopyranosyluronate)-(1 --> 4)-[(2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranosyl)-(1 --> 4)-(sodium 2,3-di-O-methyl-alpha-L-idopyranosyluronate)-(1 --> 4)](2)-2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranoside, obtainable from a single disaccharide building block precursor, constitutes a good starting point for obtaining simple oligosaccharidic heparin mimetics able to inhibit the two coagulation factors thrombin and Factor Xa. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00067-1
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 ethyl 2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-1-thio-L-idopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 methyl(2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Identification of a hexasaccharide sequence able to inhibit thrombin and suitable for ‘polymerisation’

  摘要：

  Three hexasaccharides, having from low to very high affinity for antithrombin, were synthesised from disaccharide building block precursors. One of them, methyl(sodium 2,3-di-O-methyl-4-O-sodium sulfonato-alpha-L-idopyranosyluronate)-(1 --> 4)-[(2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranosyl)-(1 --> 4)-(sodium 2,3-di-O-methyl-alpha-L-idopyranosyluronate)-(1 --> 4)](2)-2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranoside, obtainable from a single disaccharide building block precursor, constitutes a good starting point for obtaining simple oligosaccharidic heparin mimetics able to inhibit the two coagulation factors thrombin and Factor Xa. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00067-1

文献信息

• Synthetic polysaccharides, process for their preparation and pharmaceutical compositions containing them
  申请人：——

  公开号：US20040068108A1

  公开（公告）日：2004-04-08

  Synthetic polysaccharides are disclosed containing 8-24 monosaccharide units made up of a concatenation of disaccharides consisting of a uronic acid and a hexose, wherein the hydroxyl groups of the polysaccharides are etherified with a C 1-6 alkyl group or esterified in the form of a sulpho group, each disaccharide being at least monoetherified; and salts thereof, are disclosed.

  已公开的合成多糖含有 8-24 个单糖单元，由尿酸和六糖组成的二糖连接而成，其中多糖的羟基与 C-1-6 脂肪酸基团醚化。 1-6 烷基醚化或以磺基形式酯化，每个二糖至少单醚化；以及它们的盐。
• POLYSACCHARIDES SYNTHETIQUES, PROCEDE POUR LEUR PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SANOFI-SYNTHELABO

  公开号：EP0904299B1

  公开（公告）日：2001-08-29
• US7919614B2
  申请人：——

  公开号：US7919614B2

  公开（公告）日：2011-04-05
• Identification of a hexasaccharide sequence able to inhibit thrombin and suitable for ‘polymerisation’
  作者：Philippe Duchaussoy、Guy Jaurand、Pierre-A. Driguez、Isidore Lederman、Françoise Gourvenec、Jean-M. Strassel、Philippe Sizun、Maurice Petitou、Jean-M. Herbert

  DOI：10.1016/s0008-6215(99)00067-1

  日期：1999.4

  Three hexasaccharides, having from low to very high affinity for antithrombin, were synthesised from disaccharide building block precursors. One of them, methyl(sodium 2,3-di-O-methyl-4-O-sodium sulfonato-alpha-L-idopyranosyluronate)-(1 --> 4)-[(2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranosyl)-(1 --> 4)-(sodium 2,3-di-O-methyl-alpha-L-idopyranosyluronate)-(1 --> 4)](2)-2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranoside, obtainable from a single disaccharide building block precursor, constitutes a good starting point for obtaining simple oligosaccharidic heparin mimetics able to inhibit the two coagulation factors thrombin and Factor Xa. (C) 1999 Elsevier Science Ltd. All rights reserved.