allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate | 245110-06-9

• 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: allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate
• CAS: 245110-06-9
• 化学式: C₃₉H₄₅N₃O₁₂
• 分子量: 747.799
• InChiKey: RYTFWTGTJKWGBZ-NMDPSYTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  54.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  186.2
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate 在 三乙胺三氧化硫 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以78%的产率得到allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-2-O-sulfo-α-L-idopyranosiduronate sodium salt
  参考文献：
  名称：

  Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides

  摘要：

  The chemical synthesis of disaccharides 1 and 2, useful building-blocks for the preparation of a new series of heparin related oligosaccharides containing the unusual sequence (GlcN-IdoA)(n), is described. In addition, the orthogonality of the protective groups would allow access to a wide array of differently sulfated oligosaccharides. As the simplest members of this new class of oligomer, the synthesis of sulfated disaccharides 3 and 4 fully deprotected is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00526-8
• 作为产物：
  描述：

  thexyldimethylsilyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 硫酸 、 叔丁基二甲硅基三氟甲磺酸酯 、 四丁基氟化铵 、 sodium methylate 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 71.5h， 生成 allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate
  参考文献：
  名称：

  Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides

  摘要：

  The chemical synthesis of disaccharides 1 and 2, useful building-blocks for the preparation of a new series of heparin related oligosaccharides containing the unusual sequence (GlcN-IdoA)(n), is described. In addition, the orthogonality of the protective groups would allow access to a wide array of differently sulfated oligosaccharides. As the simplest members of this new class of oligomer, the synthesis of sulfated disaccharides 3 and 4 fully deprotected is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00526-8