(2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester | 192505-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• 英文别名: benzyl (2S,3S,4S,5R)-3-[[(2R,3S,4R,5R,6R)-6-(acetyloxymethyl)-3,4,5-trimethoxyoxan-2-yl]methyl]-4,5-dimethoxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate
• CAS: 192505-52-5
• 化学式: C₂₉H₄₀Cl₃NO₁₂
• 分子量: 700.995
• InChiKey: XFSLUMMVURHAFB-BQGLFUSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester 在 三氟甲磺酸三甲基硅酯 、 硫酸 、 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological activity of a new anti-factor Xa pentasaccharide with a C-interglycosidic bond

  摘要：

  A mixed synthetic C, O-pentasaccharide 17 has been synthesized and shown to display an anti-factor Xa activity similar to that of the corresponding O-pentasaccharide 18. 17 represents the first example of a synthetic C-oligosaccharidic mimetic eliciting a significant biological response. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00252-7
• 作为产物：
  描述：

  phenyl 2,4,6-tri-O-Acetyl-3-O-methyl-1-seleno-β-D-glucopyranoside 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 偶氮二异丁腈 、 氢氟酸 、 三正丁基氢锡 、 sodium methylate 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 APTS 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis and biological activity of a new anti-factor Xa pentasaccharide with a C-interglycosidic bond

  摘要：

  A mixed synthetic C, O-pentasaccharide 17 has been synthesized and shown to display an anti-factor Xa activity similar to that of the corresponding O-pentasaccharide 18. 17 represents the first example of a synthetic C-oligosaccharidic mimetic eliciting a significant biological response. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00252-7

文献信息

• Introducing a C -interglycosidic bond in a biologically active pentasaccharide hardly affects its biological properties
  作者：Maurice Petitou、Jean-Pascal Hérault、Jean-Claude Lormeau、Arnim Helmboldt、Jean-Maurice Mallet、Pierre Sinaÿ、Jean-Marc Herbert

  DOI：10.1016/s0968-0896(98)00094-7

  日期：1998.9

  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.