(3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1->4)-(6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl) trichloroacetimidate | 213899-62-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1->4)-(6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl) trichloroacetimidate
• CAS: 213899-62-8
• 化学式: C₅₀H₅₁Cl₃N₂O₁₈
• 分子量: 1074.32
• InChiKey: SDNYQRODXALCCJ-WNOSXECJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  73.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  248.11
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glycopyranosyl)-(1->4)-(6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranosyl-(1->3)-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside 、 (3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1->4)-(6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl) trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以81%的产率得到4-methoxyphenyl (3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1->4)-(6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-(2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1->4)-(6-O-l...
  参考文献：
  名称：

  Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-d-glucosamine at the reducing end

  摘要：

  To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-0-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00116-5
• 作为产物：
  描述：

  4-methoxyphenyl O-(3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1[*]4)-6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranoside 在 ammonium cerium(IV) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 2.5h， 生成 (3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1->4)-(6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl) trichloroacetimidate
  参考文献：
  名称：

  Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-d-glucosamine at the reducing end

  摘要：

  To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-0-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00116-5

文献信息

• Halkes; Slaghek; Hyppoenen, Polish Journal of Chemistry, 1999, vol. 73, # 7, p. 1123 - 1131
  作者：Halkes、Slaghek、Hyppoenen、Kamerling、Vliegenthart

  DOI：——

  日期：——