methyl 2,3,4-tri-O-benzyl-6-thio-6-S-acetyl-α-D-mannopyranoside | 911484-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-thio-6-S-acetyl-α-D-mannopyranoside
• 英文别名: methyl 6-S-acetyl-2,3,4-tri-O-benzyl-6-deoxy-6-thio-α-D-mannopyranoside；methyl 6-S-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside；S-[[(2S,3S,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl] ethanethioate
• CAS: 911484-78-1
• 化学式: C₃₀H₃₄O₆S
• 分子量: 522.662
• InChiKey: IYJRXQRVVGWICH-ZNOUKXQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-thio-6-S-acetyl-α-D-mannopyranoside 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosid-6-yl) sulfide
  参考文献：
  名称：

  新的低聚糖类似物：非糖苷连接的硫醚桥联假二糖

  摘要：

  报道了六种二糖类似物的合成。每个假双糖由两个单糖残基组成，通过硫醚官能团非糖苷连接；描述了C 2 对称和不对称取代的实例。该合成是通过首先通过硫代乙酸酯取代磺酸酯的 SN 2 将乙酸酯保护的硫引入部分保护的碳水化合物中来实现的。硫的脱乙酰之后用另一种碳水化合物磺酸盐衍生物处理，第二次 SN 2 置换得到假双糖产物。

  DOI：

  10.1055/s-2006-947338
• 作为产物：
  描述：

  ((2R,3R,4S,5S,6S)-3,4,5-三(苄氧基)-6-甲氧基四氢-2H-吡喃-2-基)甲醇 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2,3,4-tri-O-benzyl-6-thio-6-S-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  新的低聚糖类似物：非糖苷连接的硫醚桥联假二糖

  摘要：

  报道了六种二糖类似物的合成。每个假双糖由两个单糖残基组成，通过硫醚官能团非糖苷连接；描述了C 2 对称和不对称取代的实例。该合成是通过首先通过硫代乙酸酯取代磺酸酯的 SN 2 将乙酸酯保护的硫引入部分保护的碳水化合物中来实现的。硫的脱乙酰之后用另一种碳水化合物磺酸盐衍生物处理，第二次 SN 2 置换得到假双糖产物。

  DOI：

  10.1055/s-2006-947338

文献信息

• Non-Glycosidically Linked Pseudodisaccharides: Thioethers, Sulfoxides, Sulfones, Ethers, Selenoethers, and Their Binding to Lectins
  作者：Ian Cumpstey、Clinton Ramstadius、Tashfeen Akhtar、Irwin J. Goldstein、Harry C. Winter

  DOI：10.1002/ejoc.200901481

  日期：2010.4

  Hydrolytically stable non-glycosidically linked tail-to-tail pseudodisaccharides are linked by a single bridging atom remote from the anomeric centre of the constituent monosaccharides. Some such pseudodisaccharides with sulfur or oxygen bridges were found to act as disaccharide mimetics in their binding to the Banana Lectin and to Concanavalin A. A versatile synthetic route to a small library of such

  水解稳定的非糖苷连接的尾对尾假二糖通过远离组成单糖的异头中心的单个桥原子连接。发现一些具有硫桥或氧桥的此类假二糖在与香蕉凝集素和刀豆球蛋白 A 结合时充当二糖模拟物。描述了一种合成此类化合物的小型文库的通用途径。
• Synthesis and binding affinity analysis of α1-2- and α1-6- O / S -linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors
  作者：Oscar Norberg、Bin Wu、Niranjan Thota、Jian-Tao Ge、Germain Fauquet、Ann-Kathrin Saur、Teodor Aastrup、Hai Dong、Mingdi Yan、Olof Ramström

  DOI：10.1016/j.carres.2017.09.015

  日期：2017.11

  The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. (C) 2017 Elsevier Ltd. All rights reserved.
• Efficient synthesis of (6-deoxy-glycopyranosid-6-yl) sulfone derivatives and their effect on Ca2+-ATPase
  作者：Chinmoy Mukherjee、Swatilekha Ghosh、Pinki Nandi、Parimal C. Sen、Anup Kumar Misra

  DOI：10.1016/j.ejmech.2010.09.069

  日期：2010.12

  Synthesis of a series of novel (6-deoxy-glycopyranosid-6-yl) sulfone derivatives has been achieved using a general synthetic strategy. Yields were excellent in every case. The synthetic compounds were evaluated for their biological potential against Ca2+-ATPase, an important enzyme involves in tranporting Ca2+ across the cell membranes. (C) 2010 Elsevier Masson SAS. All rights reserved.
• New Oligosaccharide Analogues: Non-Glycosidically Linked Thioether-­Bridged Pseudodisaccharides
  作者：Ian Cumpstey

  DOI：10.1055/s-2006-947338

  日期：2006.7

  The synthesis of six disaccharide analogues is reported. The pseudodisaccharides each consist of two monosaccharide residues linked non-glycosidically via a thioether functionality; both C 2 -symmetric and unsymmetrically substituted examples are described. The synthesis was achieved by first introducing an acetate-protected sulfur into partially protected carbohydrates by S N 2 displacement of sulfonate

  报道了六种二糖类似物的合成。每个假双糖由两个单糖残基组成，通过硫醚官能团非糖苷连接；描述了C 2 对称和不对称取代的实例。该合成是通过首先通过硫代乙酸酯取代磺酸酯的 SN 2 将乙酸酯保护的硫引入部分保护的碳水化合物中来实现的。硫的脱乙酰之后用另一种碳水化合物磺酸盐衍生物处理，第二次 SN 2 置换得到假双糖产物。