p-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside | 488092-62-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
• CAS: 488092-62-2
• 化学式: C₆₁H₅₂O₁₈
• 分子量: 1073.07
• InChiKey: TYWUMJWRDUKHPR-CGVYLCPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.89
• 重原子数：
  79.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  224.18
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 、 p-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 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55%的产率得到p-methoxyphenyl (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-galactopyranoside
  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：

  4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 二正丁基氧化锡 、 palladium dichloride 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 p-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  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