allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronate | 245109-89-1

• 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-2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronate
• 英文别名: methyl (2R,3S,4S,5R,6R)-5-acetyloxy-3-[(2R,3R,4R,5S,6R)-6-(acetyloxymethyl)-3-azido-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-4-phenylmethoxy-6-prop-2-enoxyoxane-2-carboxylate
• CAS: 245109-89-1
• 化学式: C₄₁H₄₇N₃O₁₃
• 分子量: 789.836
• InChiKey: HBLWGCMNALHBOR-XKFDZGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  57
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  15

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-2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronate 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium methylate 、 三乙胺三氧化硫 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成
  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 chromium(VI) oxide 、 硫酸 、 叔丁基二甲硅基三氟甲磺酸酯 、 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 60.5h， 生成 allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-2-O-acetyl-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

文献信息

• A Rational Approach to Heparin-Related Fragments − Synthesis of Differently Sulfated Tetrasaccharides as Potential Ligands for Fibroblast Growth Factors
  作者：Laura Poletti、Martin Fleischer、Christian Vogel、Marco Guerrini、Giangiacomo Torri、Luigi Lay

  DOI：10.1002/1099-0690(200107)2001:14<2727::aid-ejoc2727>3.0.co;2-8

  日期：2001.7

  Heparin-like tetrasaccharides 1−3, differing in their sulfation pattern at position 6 of the glucosamine units, were synthesised. The three compounds are putative ligands for fibroblast growth factors and have the unusual sequence (GlcN-IdoA). They were obtained from two common disaccharide precursors by a versatile synthetic procedure.

  合成了在葡糖胺单元的6位的硫酸化方式不同的类肝素样四糖1-3。这三种化合物是成纤维细胞生长因子的推定配体，并具有不同寻常的序列（GlcN-IdoA）。它们是通过一种通用的合成方法从两种常见的二糖前体中获得的。