ethylthio 6-O-(2-(azidomethyl)benzoyl)-2-O-benzoyl-4-O-benzyl-3-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside | 1259036-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethylthio 6-O-(2-(azidomethyl)benzoyl)-2-O-benzoyl-4-O-benzyl-3-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside
• 英文别名: 6-O-(2-(azidomethyl)benzoyl)-2-O-benzoyl-4-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• CAS: 1259036-11-7
• 化学式: C₃₆H₄₅N₃O₇SSi
• 分子量: 691.921
• InChiKey: HQGSJMCCYMIOLZ-DVIRIBEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  48.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  129.05
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethylthio 6-O-(2-(azidomethyl)benzoyl)-2-O-benzoyl-4-O-benzyl-3-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 1.17h， 生成 6-O-(2-(azidomethyl)benzoyl)-2-O-benzoyl-4-O-benzyl-3-O-(tert-butyldimethylsilyl)-β-D-glucopyranose 、 6-O-(2-(azidomethyl)benzoyl)-2-O-benzoyl-4-O-benzyl-3-O-(tert-butyldimethylsilyl)-β-D-glucopyranose
  参考文献：
  名称：

  β(1,3) Branched heptadeca- and linear hexadeca-saccharides possessing an aminoalkyl group as a strong ligand to dectin-1

  摘要：

  在本报告中，我们描述了含有氨基烷基团的β(1,3)低聚糖的汇聚合成。分支的十七糖和线性的十六糖作为dectin-1的配体，其结合亲和力仅比天然SPG弱10倍，并展现出dectin-1激动剂活性。

  DOI：

  10.1039/c0cc03153d
• 作为产物：
  描述：

  2-(azidomethyl)benzoyl chloride 、 ethylthio 2-O-benzoyl-4-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到ethylthio 6-O-(2-(azidomethyl)benzoyl)-2-O-benzoyl-4-O-benzyl-3-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside
  参考文献：
  名称：

  β(1,3) Branched heptadeca- and linear hexadeca-saccharides possessing an aminoalkyl group as a strong ligand to dectin-1

  摘要：

  在本报告中，我们描述了含有氨基烷基团的β(1,3)低聚糖的汇聚合成。分支的十七糖和线性的十六糖作为dectin-1的配体，其结合亲和力仅比天然SPG弱10倍，并展现出dectin-1激动剂活性。

  DOI：

  10.1039/c0cc03153d

文献信息

• Synthesis of β(1,3) oligoglucans exhibiting a Dectin-1 binding affinity and their biological evaluation
  作者：Hiroshi Tanaka、Tetsuya Kawai、Yoshiyuki Adachi、Shinya Hanashima、Yoshiki Yamaguchi、Naohito Ohno、Takashi Takahashi

  DOI：10.1016/j.bmc.2012.04.017

  日期：2012.6

  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.