ethylthio 4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranoside | 1259036-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethylthio 4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aR)-6-ethylsulfanyl-7-(4-oxopentanoyloxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 4-oxopentanoate
• CAS: 1259036-06-0
• 化学式: C₂₅H₃₂O₉S
• 分子量: 508.59
• InChiKey: LTDSXCSNTIXREI-WLAPLSBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethylthio 4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-[(1R,3R,7R,8S,9S,11R)-8-hydroxy-5-methoxy-11-phenyl-2,4,6,10,12-pentaoxatricyclo[7.4.0.03,7]tridecan-5-yl]butan-2-one
  参考文献：
  名称：

  N-聚糖核心三糖的便捷合成

  摘要：

  描述了N-聚糖的核心三糖的方便合成。进行三个单糖结构单元的正交一锅糖基化反应以提供β-葡萄糖基壳二糖，然后通过分子内差向异构化β-葡萄糖苷的C-2位将其转化为β-甘露糖基壳二糖。遵循4，6 - O-亚苄基保护的1，2-原酸酯策略，制备了具有分化的2，3-OH的关键葡糖基供体7c。

  DOI：

  10.1016/j.tetlet.2011.04.060
• 作为产物：
  描述：

  乙酰丙酸 、 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到ethylthio 4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranoside
  参考文献：
  名称：

  N-聚糖核心三糖的便捷合成

  摘要：

  描述了N-聚糖的核心三糖的方便合成。进行三个单糖结构单元的正交一锅糖基化反应以提供β-葡萄糖基壳二糖，然后通过分子内差向异构化β-葡萄糖苷的C-2位将其转化为β-甘露糖基壳二糖。遵循4，6 - O-亚苄基保护的1，2-原酸酯策略，制备了具有分化的2，3-OH的关键葡糖基供体7c。

  DOI：

  10.1016/j.tetlet.2011.04.060

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.
• A convenient synthesis of the core trisaccharide of the N-glycans
  作者：Zhichao Lu、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li

  DOI：10.1016/j.tetlet.2011.04.060

  日期：2011.6

  A convenient synthesis of the core trisaccharide of the N-glycans was described. Orthogonal one-pot glycosylation of three monosaccharide building blocks was performed to furnish β-glucosyl chitobiose, which was then transformed to β-mannosyl chitobiose by intramolecular epimerization of the C-2 position of the β-glucoside. The key glucosyl donor 7c with differentiated 2,3-OH was prepared following

  描述了N-聚糖的核心三糖的方便合成。进行三个单糖结构单元的正交一锅糖基化反应以提供β-葡萄糖基壳二糖，然后通过分子内差向异构化β-葡萄糖苷的C-2位将其转化为β-甘露糖基壳二糖。遵循4，6 - O-亚苄基保护的1，2-原酸酯策略，制备了具有分化的2，3-OH的关键葡糖基供体7c。