benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5R,6R)-4,5-dimethoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenylmethoxycarbonyloxan-3-yl]oxy-5-phenylmethoxyoxan-3-yl]oxy-3-hydroxy-4,5-dimethoxyoxane-2-carboxylate | 175722-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5R,6R)-4,5-dimethoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenylmethoxycarbonyloxan-3-yl]oxy-5-phenylmethoxyoxan-3-yl]oxy-3-hydroxy-4,5-dimethoxyoxane-2-carboxylate
• CAS: 175722-90-4
• 化学式: C₇₅H₈₈O₂₅
• 分子量: 1389.51
• InChiKey: SELNHCUISIKEFO-QWAKXKTASA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  100
• 可旋转键数：
  37
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  273
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5R,6R)-4,5-dimethoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenylmethoxycarbonyloxan-3-yl]oxy-5-phenylmethoxyoxan-3-yl]oxy-3-hydroxy-4,5-dimethoxyoxane-2-carboxylate 、 Acetic acid (2R,3R,4S,5R)-3-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl ester 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到
  参考文献：
  名称：

  Westerduin, Pieter; Basten, Jan E. M.; Broekhoven, Marc A., Angewandte Chemie, 1996, vol. 108, # 3, p. 339 - 342

  摘要：

  DOI：
• 作为产物：
  描述：

  在 乙酸肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5R,6R)-4,5-dimethoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenylmethoxycarbonyloxan-3-yl]oxy-5-phenylmethoxyoxan-3-yl]oxy-3-hydroxy-4,5-dimethoxyoxane-2-carboxylate
  参考文献：
  名称：

  Experimental Proof for the Structure of a Thrombin-Inhibiting Heparin Molecule

  摘要：

  Kinetic studies of thrombin inhibition by antithrombin in the presence of heparin have shown that thrombin binds to heparin in a preformed heparin - antithrombin complex. To study the relative position of the thrombin binding domain and the antithrombin binding domain on a heparin molecule we have designed and synthesized heparin mimetics which structurally are very similar to the genuine polysaccharide. Their inhibitory properties with respect to factor Xa and thrombin provide experimental evidence that in heparin the thrombin binding domain must be located at the nonreducing end of the antithrombin binding domain to observe thrombin inhibition. As expected, factor Xa inhibition is not affected by elongation of the antithrombin binding pentasaccharide sequence, regardless of the position in which this elongation takes place.

  DOI：

  10.1002/1521-3765(20010216)7:4<858::aid-chem858>3.0.co;2-n

文献信息

• Novel polysaccharides with antithrombotic activity comprising at least one covalent bond with biotin or a biotin derivative
  申请人：Duchaussoy Philippe

  公开号：US20060160768A1

  公开（公告）日：2006-07-20

  The present invention relates to novel synthetic polysaccharides with antithrombotic activity exhibiting at least one covalent bond with biotin or a biotin derivative and to a process employing avidin or streptavidin which makes it possible to neutralize these polysaccharides.

  本发明涉及具有抗血栓活性的新型合成多糖，其至少与生物素或生物素衍生物之一形成共价键，以及利用亲和素或链球菌素的过程，使得可以中和这些多糖。
• New synthetic heparin mimetics able to inhibit thrombin and factor Xa
  作者：Maurice Petitou、Philippe Duchaussoy、Pierre-A. Driguez、Jean-P. Hérault、Jean-C. Lormeau、Jean-M. Herbert

  DOI：10.1016/s0960-894x(99)00155-9

  日期：1999.4

  Synthetic pentadeca-, heptadeca- and nonadecasaccharides, comprising an antithrombin III (AT III) binding pentasaccharide prolonged at the non-reducing end by a thrombin binding domain have been obtained. The pentadecasaccharide is the shortest oligosaccharide able to catalyse thrombin inhibition by AT III. The nonadecasaccharide is a more potent thrombin inhibitor than standard heparin. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Synthetic Carbohydrate Derivatives as Low Sulfated Heparin Mimetics
  作者：Pierre-A. Driguez、Isidore Lederman、Jean-M. Strassel、Jean-M. Herbert、Maurice Petitou

  DOI：10.1021/jo991152j

  日期：1999.12.1

  The total synthesis of a new family of heparin mimetics containing an hexadeca- (2), an octadeca- (3), and an eicosasaccharide (4) is described. All three oligosaccharides contain a pentasaccharidic antithrombin binding domain(DEFGH: van Boeckel, C. A. A.; Petitou, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1671-1690), extended at the nonreducing end by a thrombin binding domain composed of repeated 2,3-di-O-methyl-6-O-sodium sulfonato-alpha-D-glucosyl units, The targets were synthesized using a key dodecasaccharide imidate as glycosyl donor as well as di- and tetrasaccharide imidates, all derived from maltose. Condensation of these imidates with a tetrasaccharide precursor of the EFGH part of the antithrombin binding domain gave fully protected hexadeca-, octadeca-, and eicosasaccharide that were deprotected and sulfated to yield 2, 3, and 4. All three displayed antithrombin-mediated antifactor Xa and antithrombin (factor IIa) activity. The most active compound, the eicosasaccharide, showed activity similar to that of low molecular weight heparin. Significantly, unlike heparin and its derivatives, the present: heparin mimetics do not interact with platelet factor 4, an interaction that can cause severe side effects in heparin-treated patients. Thus, this new family of compounds contains interesting drug candidates for the prevention and treatment of thrombosis.