methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside | 488092-65-5

• 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-acetyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside
• CAS: 488092-65-5
• 化学式: C₈₇H₈₀O₃₂
• 分子量: 1637.57
• InChiKey: SQCWYRPZWMBBLD-KUGBZULQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.36
• 重原子数：
  119.0
• 可旋转键数：
  29.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  389.44
• 氢给体数：
  0.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以80%的产率得到methyl (β-D-glucopyranosyluronic acid)-(1->3)-β-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-xylopyranoside, sodium salt
  参考文献：
  名称：

  A practical synthesis of β-d-GlcA-(1→3)-β-d-Gal-(1→3)-β-d-Gal-(1→4)-d-Xyl, a part of the common linkage region of a glycosaminoglycan

  摘要：

  A practical synthesis of beta-D-GlcA-(1 --> 3)-beta-D-Gal-(1 --> 3)-beta-D-Gal-(1 -->4)-beta-D-Xyl-(1 --> OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-beta-D-xylopyranoside, followed by deallylation. The beta-(1 --> 3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside as the key synthon. The alpha-(1--> 3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation. CO 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00169-6
• 作为产物：
  描述：

  methyl 2,3-di-O-benzoyl-β-D-xylopyranoside 、 (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以40%的产率得到methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside
  参考文献：
  名称：

  A practical synthesis of β-d-GlcA-(1→3)-β-d-Gal-(1→3)-β-d-Gal-(1→4)-d-Xyl, a part of the common linkage region of a glycosaminoglycan

  摘要：

  A practical synthesis of beta-D-GlcA-(1 --> 3)-beta-D-Gal-(1 --> 3)-beta-D-Gal-(1 -->4)-beta-D-Xyl-(1 --> OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-beta-D-xylopyranoside, followed by deallylation. The beta-(1 --> 3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside as the key synthon. The alpha-(1--> 3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation. CO 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00169-6