methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate | 275824-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate
• CAS: 275824-46-9
• 化学式: C₃₇H₃₆Cl₆N₂O₁₇
• 分子量: 993.414
• InChiKey: PHCDXKVHYWIJMV-LVYFQLIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  62.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  247.67
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  methyl (4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 、 methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β..
  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 (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 在 ammonium cerium(IV) nitrate 、 1,5-Diazabicyclo[5.4.0]undec-5-ene 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 1.75h， 生成 methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate
  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