2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-galactopyranosyl trichloroacetimidate | 666263-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
• CAS: 666263-31-6
• 化学式: C₈₀H₆₈Cl₃NO₂₆
• 分子量: 1565.77
• InChiKey: GUJRIWMNBWQUCJ-DSDSOVAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.86
• 重原子数：
  110.0
• 可旋转键数：
  26.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  342.23
• 氢给体数：
  1.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-galactopyranosyl trichloroacetimidate 、 lauryl 2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glucopyranoside 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25%的产率得到
  参考文献：
  名称：

  Synthesis of galactose-containing analogues of (1→6)-branched (1→3)-glucohexaose and its lauryl glycoside

  摘要：

  Coupling of the trisaccharide acceptor either 2,4,6-tri-O-acetyl-beta-D-glucopyranosyl-(1 -> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 -> 6)]-5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranose (13) or lauryl 2,4,6-tri-O-acetyl-beta-D-glucopyranosyl(1 -> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 -> 6)]-2,5-di-O-acetyl-alpha-D-glucopyranoside (15) with the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 -> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 -> 6)]-2,4-di-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate (12) gave alpha-linked hexasaccharides 14 and 16, respectively, while coupling of either 13 or 15 with trisaccharide donor 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1 -> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1 -> 6)]-2,4-di-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate 17 did not afford any hexasaccarides. The analogues of the immunomodulator beta-D-Glcp-(1 -> 3)-[beta-D-Glcp-(1 -> 6)]-beta-D-Glcp-(1 -> 3)-beta-D-Glcp-beta-(1 -> 3)-[beta-D-Glcp-(1 -> 6)]-beta-D-Glcp (1) was obtained by deprotection of 14 and 16. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.01.011
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-galactofuranose 、 乙酸酐 、 三氯乙腈 以71%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of galactose-containing analogues of (1→6)-branched (1→3)-glucohexaose and its lauryl glycoside

  摘要：

  Coupling of the trisaccharide acceptor either 2,4,6-tri-O-acetyl-beta-D-glucopyranosyl-(1 -> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 -> 6)]-5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranose (13) or lauryl 2,4,6-tri-O-acetyl-beta-D-glucopyranosyl(1 -> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 -> 6)]-2,5-di-O-acetyl-alpha-D-glucopyranoside (15) with the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 -> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 -> 6)]-2,4-di-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate (12) gave alpha-linked hexasaccharides 14 and 16, respectively, while coupling of either 13 or 15 with trisaccharide donor 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1 -> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1 -> 6)]-2,4-di-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate 17 did not afford any hexasaccarides. The analogues of the immunomodulator beta-D-Glcp-(1 -> 3)-[beta-D-Glcp-(1 -> 6)]-beta-D-Glcp-(1 -> 3)-beta-D-Glcp-beta-(1 -> 3)-[beta-D-Glcp-(1 -> 6)]-beta-D-Glcp (1) was obtained by deprotection of 14 and 16. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.01.011