1,6:2,3-dianhydro-4-O-(tetrahydropyran-2-yl)-β-D-mannopyranose | 67313-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 1,6:2,3-dianhydro-4-O-(tetrahydropyran-2-yl)-β-D-mannopyranose
• 英文别名: (1R,2S,4S,5R,6R)-5-(oxan-2-yloxy)-3,8,9-trioxatricyclo[4.2.1.02,4]nonane
• CAS: 67313-50-2
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: MQDIDUHQHGGADN-QTFFHLKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.45
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,6:2,3-dianhydro-4-O-(tetrahydropyran-2-yl)-β-D-mannopyranose 在 盐酸 、 水 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.08h， 生成 1,6-anhydro-2-O-butyl-3-O-methyl-β-D-glucopyranose
  参考文献：
  名称：

  [EN] FGF RECEPTOR-ACTIVATING 3-O-ALKYL OLIGOSACCHARIDES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF
  [FR] 3-O-ALKYL-OLIGOSACCHARIDES ACTIVATEURS DE RÉCEPTEUR FGF, PRÉPARATION DE CEUX-CI ET UTILISATION THÉRAPEUTIQUE DE CEUX-CI

  摘要：

  该发明涉及与式（I）中R1代表可选择地取代的-O-烷基基团，R2代表羟基或-O-烷基基团，R3、R5、R6、R7和R8代表-OSO3-或羟基，R4代表NH-CO-烷基或-O-烷基基团，R代表-O-烷基基团，n和m，可以相同也可以不同，代表整数0或1的FGF受体激活寡糖。其制备方法和治疗用途。

  公开号：

  WO2012101605A1

文献信息

• Azasugar derivatives, heparanase inhibitors, method for preparing same, compositions containing same, use thereof
  申请人：PETITOU Maurice

  公开号：US20070270354A1

  公开（公告）日：2007-11-22

  The invention concerns heparanase inhibiting compounds of general formula (I) wherein R represents a hydrogen atom, an hydroxyl radical, a —OSO 3 − radical, a —O—(C 1 -C 5 )alkyl radical or an —O— aralkyl radical; Z represents a COO − radical or a hydroxyl radical; X represents —OH or a saccharide unit of formula A, Y represents H, C 1 -C 5 alkyl or a saccharide unit of formula D; in free form or in the form of pharmaceutically acceptable salts formed with a base or an acid as well as in the form of solvates or hydrates. The derivatives of the invention are useful as medicines.

  该发明涉及通式（I）的肝素酶抑制化合物，其中R代表氢原子、羟基自由基、—OSO3−自由基、—O—（C1-C5）烷基自由基或—O—芳基烷基自由基；Z代表COO−自由基或羟基自由基；X代表—OH或通式A的糖单元；Y代表H、C1-C5烷基或通式D的糖单元；以游离形式或形成与碱或酸的药用可接受盐、溶剂化合物或水合物的形式存在。该发明的衍生物可用作药物。
• Total synthesis of a heparin pentasaccharide fragment having high affinity for antithrombin III
  作者：Pierre Sinaÿ、Jean-Claude Jacquinet、Maurice Petitou、Philippe Duchaussoy、Isidore Lederman、Jean Choay、Giangiacomo Torri

  DOI：10.1016/0008-6215(84)85236-2

  日期：1984.9
• Synthesis and biological activity of a new anti-factor Xa pentasaccharide with a C-interglycosidic bond
  作者：Arnim Helmboldt、Maurice Petitou、Jean-Maurice Mallet、Jean-Pascal Hérault、Jean-Claude Lormeau、Pierre Alexandre Driguez、Jean-Marc Herbert、Pierre Sinaÿ

  DOI：10.1016/s0960-894x(97)00252-7

  日期：1997.6

  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.
• 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.
• WESSEL, HANS PETER;LABLER, LUDVIK;TSCHOPP, THOMAS B., HELV. CHIM. ACTA, 72,(1989) N, C. 1268-1277
  作者：WESSEL, HANS PETER、LABLER, LUDVIK、TSCHOPP, THOMAS B.

  DOI：——

  日期：——