4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>4)-2,3-di-O-p-toluoyl-β-D-glucopyranoside | 167013-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>4)-2,3-di-O-p-toluoyl-β-D-glucopyranoside
• CAS: 167013-85-6
• 化学式: C₄₉H₄₉NO₁₈
• 分子量: 939.924
• InChiKey: GZIFWWVIBREAMG-QGXRZILUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  68.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  235.26
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>4)-2,3-di-O-p-toluoyl-β-D-glucopyranoside 在 sodium chlorite 、 草酰氯 、 camphor-10-sulfonic acid 、 二甲基亚砜 、 甲胺 作用下， 以 甲醇 为溶剂， 反应 74.5h， 生成 4-methoxyphenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranosyluronic acid
  参考文献：
  名称：

  Synthesis of hyaluronic acid related di- and tetra-saccharides having a glucuronic acid at the reducing end

  摘要：

  The synthesis is reported of 4-methoxyphenyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-beta-D-glucopyranosyluronic acid (1) and 4-methoxyphenyl O-2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-O-(beta-D-glucopyranosyluronic acid)-(1-->3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)- (1-->4-beta-D-glucopyranosyluronic acid (5), which represent structural elements of hyaluronic acid. 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate (3) was condensed with 4-methoxyphenyl 6-O-levulinoyl-2,3-di-O-p-toluoyl-beta-D-glucopyranoside (4) in dichloromethane, using boron trifluoride etherate as a promoter, yielding 4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D- glucopyranosylyl)-(1-->4)6-O-levulinoyl-2,3-di-O-p-toluoyl-beta-D-glucopyranoside (2). Subsequent delevulinoylation, oxidation, complete deprotection, and N-acetylation gave 1. Coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido- beta-D-glucopyranosyl trichloroacetimidate (9) with 4, followed by de-allyloxycarbonylation of the obtained disaccharide derivative gave 4-methoxyphenyl O-(2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D- glucopyranosyl)-(1-->4)-6-O-levulinoyl-2,3-di-O-p-toloyl-beta-D-glucopyranoside (8). Demethoxyphenylation and subsequent imidation of 2 afforded O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D- glucopyranosyl)-(1-->4)-6-O-levulinoyl-2,3-di-O-p-toluoyl-alpha/beta-D-glucopyranosylucopyranosyl trichloroacetimidate (7). Condensation of 7 and 8 in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave tetrasaccharide derivative 15. Subsequent de-isopropylidenation, O-acetylation, delevulinoylation, oxidation, complete deprotection, and N-acetylation yielded 5.

  DOI：

  10.1016/s0957-4166(00)86307-7
• 作为产物：
  描述：

  4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>4)-6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranoside 在 乙酸肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 0.67h， 以86%的产率得到4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>4)-2,3-di-O-p-toluoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of hyaluronic acid related di- and tetra-saccharides having a glucuronic acid at the reducing end

  摘要：

  The synthesis is reported of 4-methoxyphenyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-beta-D-glucopyranosyluronic acid (1) and 4-methoxyphenyl O-2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-O-(beta-D-glucopyranosyluronic acid)-(1-->3)-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)- (1-->4-beta-D-glucopyranosyluronic acid (5), which represent structural elements of hyaluronic acid. 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate (3) was condensed with 4-methoxyphenyl 6-O-levulinoyl-2,3-di-O-p-toluoyl-beta-D-glucopyranoside (4) in dichloromethane, using boron trifluoride etherate as a promoter, yielding 4-methoxyphenyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D- glucopyranosylyl)-(1-->4)6-O-levulinoyl-2,3-di-O-p-toluoyl-beta-D-glucopyranoside (2). Subsequent delevulinoylation, oxidation, complete deprotection, and N-acetylation gave 1. Coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido- beta-D-glucopyranosyl trichloroacetimidate (9) with 4, followed by de-allyloxycarbonylation of the obtained disaccharide derivative gave 4-methoxyphenyl O-(2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D- glucopyranosyl)-(1-->4)-6-O-levulinoyl-2,3-di-O-p-toloyl-beta-D-glucopyranoside (8). Demethoxyphenylation and subsequent imidation of 2 afforded O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D- glucopyranosyl)-(1-->4)-6-O-levulinoyl-2,3-di-O-p-toluoyl-alpha/beta-D-glucopyranosylucopyranosyl trichloroacetimidate (7). Condensation of 7 and 8 in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave tetrasaccharide derivative 15. Subsequent de-isopropylidenation, O-acetylation, delevulinoylation, oxidation, complete deprotection, and N-acetylation yielded 5.

  DOI：

  10.1016/s0957-4166(00)86307-7