methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosid)uronate | 156977-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosid)uronate
• 英文别名: methyl (2R,3S,4S,5R,6R)-5-acetyloxy-3-hydroxy-6-methoxy-4-phenylmethoxyoxane-2-carboxylate
• CAS: 156977-42-3
• 化学式: C₁₇H₂₂O₈
• 分子量: 354.357
• InChiKey: DGXQQCLTOMGRLM-DEQQHWRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosid)uronate 在 palladium on activated charcoal sodium hydroxide 、 pyridine-SO3 complex 、 4 A molecular sieve 、 叔丁基二甲硅基三氟甲磺酸酯 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of heparin partial structures and their binding activities to platelets

  摘要：

  A synthetic pentasaccharide corresponding to the antithrombin III-binding region in heparin was also found to bind to human platelets. To identify the platelet-binding site in the pentasaccharide which is expected to be a novel sequence in heparin responsible for its platelet-binding, five partial structures of this particular pentasaccharide were synthesized. In a competitive assay using [H-3]-heparin, a trisaccharide, O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1-->4)-2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranose, was concluded to be a high-affinity site for heparin's binding to platelets. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00550-8
• 作为产物：
  描述：

  [(2S,3R,4S,5R)-3,5-diacetyloxy-6-hydroxy-4-phenylmethoxyoxan-2-yl]methyl acetate 在 potassium bromide 吡啶 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 四丁基氯化铵 、 水 、 sodium methylate 、 caesium carbonate 、 2,2-二甲氧基丙烷 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosid)uronate
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9

文献信息

• FGF receptor-activating N-sulfate oligosaccharides, preparation thereof, and therapeutic use thereof
  申请人：Duchaussoy Philippe

  公开号：US09527930B2

  公开（公告）日：2016-12-27

  The invention relates to FGF receptor-activating N-sulfate oligosaccharides having Formula (I), wherein R1, R4, R6, and R8 are —OSO3− or hydroxyl groups, R2 is an —O-alkyl group or a monosaccharide having Formula (II), R3 is a disaccharide having Formula (III), R5 is a disaccharide having Formula (IV), R7 is a hydroxyl group or a disaccharide having Formula (VI), and R9 is a hydroxyl or —O-alkyl group or a disaccharide having Formula (VII), where R10— is an —O-alkyl group. The invention further relates to the preparation of said oligosaccharides and to the therapeutic use thereof.

  该发明涉及具有以下结构的FGF受体激活N-磺酸寡糖，其中R1、R4、R6和R8为—OSO3−或羟基基团，R2为—O-烷基基团或具有以下结构的单糖（II），R3为具有以下结构的二糖（III），R5为具有以下结构的二糖（IV），R7为羟基基团或具有以下结构的二糖（VI），R9为羟基或—O-烷基基团或具有以下结构的二糖（VII），其中R10—为—O-烷基基团。该发明还涉及所述寡糖的制备以及其治疗用途。
• Davis, Nicola J.; Flitsch, Sabine L., Journal of the Chemical Society. Perkin transactions I, 1994, # 4, p. 359 - 368
  作者：Davis, Nicola J.、Flitsch, Sabine L.

  DOI：——

  日期：——