ethylthio 2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-3-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranoside | 1259035-95-4

• 分子结构分类: 有机化合物
• 英文名称: ethylthio 2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-3-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranoside
• CAS: 1259035-95-4
• 化学式: C₇₈H₈₂O₂₆S
• 分子量: 1467.56
• InChiKey: SRMNAAFGHJRIHC-IGHGVBSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.63
• 重原子数：
  105.0
• 可旋转键数：
  24.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  298.02
• 氢给体数：
  1.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  ethylthio 2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-3-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 0.5h， 以96%的产率得到ethylthio 2-O-benzoyl-4,6-O-benzylidene-3-O-(2-O-acetyl-4,6-O-benzylidene-3-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β(1,3) oligoglucans exhibiting a Dectin-1 binding affinity and their biological evaluation

  摘要：

  In this report, we describe the synthesis and biological evaluation of beta(1,3) oligosaccharides that contain an aminoalkyl group and their biological evaluation. A 2,3 diol glycoside with a 4,6 benzylidene protecting group was used as an effective glycosyl acceptor for the synthesis of some beta(1,3) linked glycosides. The use of a combination of a linear tetrasaccharide and a branched pentasaccharide as glycosyl donors led to the preparation of beta(1,3) linear octa-to hexadecasaccharides and branched nona-to heptadecasaccharides in good total yields. Measurements of the competitive effects of the oligosaccharides on the binding of a soluble form of Dectin-1 to a solid-supported Schizophyllan (SPG) revealed that the branched heptadecasaccharide and the linear hexadecasaccharides also have binding activity for Dectin-1. In addition, the two oligosaccharides, both of which contain a beta(1,3) hexadecasaccharide backbone, exhibited agonist activity in a luciferase-assisted NF-kappa B assay. STD-NMR analyses of complexes of Dectin-1 and the linear hexadecasaccharides clearly indicate Dectin-1 specifically recognizes the sugar part of the oligosaccharides and not the aminoalkyl chain. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.04.017
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 、 O-(2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranosyl)-D-glucopyranosyl)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 0.5h， 以90%的产率得到ethylthio 2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-3-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-(4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β(1,3) oligoglucans exhibiting a Dectin-1 binding affinity and their biological evaluation

  摘要：

  In this report, we describe the synthesis and biological evaluation of beta(1,3) oligosaccharides that contain an aminoalkyl group and their biological evaluation. A 2,3 diol glycoside with a 4,6 benzylidene protecting group was used as an effective glycosyl acceptor for the synthesis of some beta(1,3) linked glycosides. The use of a combination of a linear tetrasaccharide and a branched pentasaccharide as glycosyl donors led to the preparation of beta(1,3) linear octa-to hexadecasaccharides and branched nona-to heptadecasaccharides in good total yields. Measurements of the competitive effects of the oligosaccharides on the binding of a soluble form of Dectin-1 to a solid-supported Schizophyllan (SPG) revealed that the branched heptadecasaccharide and the linear hexadecasaccharides also have binding activity for Dectin-1. In addition, the two oligosaccharides, both of which contain a beta(1,3) hexadecasaccharide backbone, exhibited agonist activity in a luciferase-assisted NF-kappa B assay. STD-NMR analyses of complexes of Dectin-1 and the linear hexadecasaccharides clearly indicate Dectin-1 specifically recognizes the sugar part of the oligosaccharides and not the aminoalkyl chain. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.04.017