(2S,3S,4S,5R,6R)-6-((1R,2R,3S,4R,5R)-3-Acetoxy-4-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3-((2R,3S,4R,5R,6R)-6-acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester | 192505-54-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4S,5R,6R)-6-((1R,2R,3S,4R,5R)-3-Acetoxy-4-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3-((2R,3S,4R,5R,6R)-6-acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS: 192505-54-7
• 化学式: C₄₂H₅₆O₁₇
• 分子量: 832.896
• InChiKey: WWGLRNNRTQEERH-PEFJTDEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  59.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  180.43
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2S,3S,4S,5R,6R)-6-((1R,2R,3S,4R,5R)-3-Acetoxy-4-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3-((2R,3S,4R,5R,6R)-6-acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 在 硫酸 、 溶剂黄146 作用下， 反应 0.25h， 生成 、
  参考文献：
  名称：

  Introducing a C -interglycosidic bond in a biologically active pentasaccharide hardly affects its biological properties

  摘要：

  We describe here the synthesis and the biological activity of a 'C-pentasaccharide', a new analogue of the antithrombin III (AT III) binding region of heparin containing a methylene bridge in place of an interglycosidic oxygen atom. The affinity for AT III and the anti-factor Xa activity of this compound have been compared with that of the corresponding selected 'O-pentasaccharide'. Such a structural modification slightly decreased the affinity of this compound for AT III as well as its anti-factor Xa activity (880 +/- 40 anti-Xa units versus 1180 +/- 30 anti-Xa units for the C-pentasaccharide and the O-pentasaccharide, respectively). This compound therefore represents the first example of a new class of anti-factor Xa pentasaccharides containing a C-interglycosidic bond. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00094-7
• 作为产物：
  描述：

  苯甲醇钠 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 、 三乙胺 、 苯甲醇 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 (2S,3S,4S,5R,6R)-6-((1R,2R,3S,4R,5R)-3-Acetoxy-4-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3-((2R,3S,4R,5R,6R)-6-acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Introducing a C -interglycosidic bond in a biologically active pentasaccharide hardly affects its biological properties

  摘要：

  We describe here the synthesis and the biological activity of a 'C-pentasaccharide', a new analogue of the antithrombin III (AT III) binding region of heparin containing a methylene bridge in place of an interglycosidic oxygen atom. The affinity for AT III and the anti-factor Xa activity of this compound have been compared with that of the corresponding selected 'O-pentasaccharide'. Such a structural modification slightly decreased the affinity of this compound for AT III as well as its anti-factor Xa activity (880 +/- 40 anti-Xa units versus 1180 +/- 30 anti-Xa units for the C-pentasaccharide and the O-pentasaccharide, respectively). This compound therefore represents the first example of a new class of anti-factor Xa pentasaccharides containing a C-interglycosidic bond. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00094-7