methyl (methyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4-)-(methyl 2,3-di-O-... | 275824-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4-)-(methyl 2,3-di-O-...
• CAS: 275824-53-8
• 化学式: C₈₇H₈₈N₂O₃₆
• 分子量: 1737.65
• InChiKey: YRFSKDXTMPEIIS-DGCRBKQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  125.0
• 可旋转键数：
  30.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  494.42
• 氢给体数：
  6.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4-)-(methyl 2,3-di-O-... 在 三甲基铵三氧化硫共聚物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以87%的产率得到methyl (methyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(sodium 2-acetamido-2-deoxy-6-O-sulfonato-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(sodium 2-acetamido-2-deoxy-6-O-sulfonato-...
  参考文献：
  名称：

  Syntheses of chondroitin 4- and 6-sulfate pentasaccharide derivatives having a methyl β-d-glucopyranosiduronic acid at the reducing end

  摘要：

  The syntheses are reported of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpA-(1 --> OMe), O-sulfonated at C-4 or C-6 of the aminosugar moieties, which represent structural elements of chondroitin 4- and 6-sulfate proteoglycans. Starting from a synthetic disaccharide glycosyl acceptor, the stepwise or blockwise construction of the sugar backbone with appropriate synthons led to a pentasaccharide tetraol, which was used as a common intermediate. Selective 6-O-sulfonation of this tetraol, followed by saponification, gave the 6-sulfate derivative, whereas selective 6-O-benzoylation, followed by O-sulfonation and saponification, afforded the 4-sulfate derivative as their sodium salts. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00032-x
• 作为产物：
  描述：

  methyl (methyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-(4,6-O-benzylidene-2-deoxy-β-D-galacto... 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.5h， 以79%的产率得到methyl (methyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4-)-(methyl 2,3-di-O-...
  参考文献：
  名称：

  Syntheses of chondroitin 4- and 6-sulfate pentasaccharide derivatives having a methyl β-d-glucopyranosiduronic acid at the reducing end

  摘要：

  The syntheses are reported of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpA-(1 --> OMe), O-sulfonated at C-4 or C-6 of the aminosugar moieties, which represent structural elements of chondroitin 4- and 6-sulfate proteoglycans. Starting from a synthetic disaccharide glycosyl acceptor, the stepwise or blockwise construction of the sugar backbone with appropriate synthons led to a pentasaccharide tetraol, which was used as a common intermediate. Selective 6-O-sulfonation of this tetraol, followed by saponification, gave the 6-sulfate derivative, whereas selective 6-O-benzoylation, followed by O-sulfonation and saponification, afforded the 4-sulfate derivative as their sodium salts. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00032-x