methyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-disulfide | 1433190-70-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-disulfide
• 英文别名: methyl-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)disulfide；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(methyldisulfanyl)oxan-2-yl]methyl acetate
• CAS: 1433190-70-5
• 化学式: C₁₅H₂₂O₉S₂
• 分子量: 410.466
• InChiKey: VZMVWNZSQPPGPA-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 methyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-disulfide
  参考文献：
  名称：

  Exploring the Native Chemical Ligation Concept for Highly Stereospecific Glycosylation Reactions

  摘要：

  Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlled activating system. To explain the origin of stereoselective preference, an S(N)i mechanism was proposed and corroborated by computational calculations.

  DOI：

  10.1021/jo400020q

文献信息

• Novel strategies for the synthesis of unsymmetrical glycosyl disulfides
  作者：Goreti Ribeiro Morais、Bradley R. Springett、Martin Pauze、Lisa Schröder、Matthew Northrop、Robert A. Falconer

  DOI：10.1039/c6ob00230g

  日期：——

  Novel strategies for the efficient synthesis of unsymmetrical glycosyl disulfides are reported. Glycosyl disulfides are increasingly important as glycomimetics and molecular probes in glycobiology. Sialosyl disulfides are synthesised directly from the chlorosialoside Neu5Ac2Cl, proceeding via a thiol-disulfide exchange reaction between the sialosyl thiolate and symmetrical disulfides. This methodology

  报道了有效合成不对称糖基二硫化物的新策略。糖基二硫化物作为糖模拟物和糖生物学中的分子探针越来越重要。唾液酸基二硫化物直接由氯唾液酸Neu5Ac2Cl合成，并通过唾液酸硫醇盐和对称的二硫化物之间的硫醇-二硫键交换反应进行。对该方法进行了修改，发现可成功地在温和条件下用于合成不对称的葡萄糖基二硫化物。
• Synthesis of mixed glycosyl disulfides/selenenylsulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent
  作者：Cheerladinne Venkateswarlu、Vibha Gautam、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2014.09.005

  日期：2015.1

  An easy and mild method has been developed for the synthesis of mixed glycosyl disulfides/selenenylsulfides from glycosyl halides and diaryl/dialkyl dichalcogenides in the presence of benzyltriethylammonium tetrathiomolybdate [(BnEt3N)(2)MoS4]. The salient feature of this method is the sulfur transfer from [BnEt3N](2)MoS4 to form glycosyl disulfides which with excess tetrathiomolybdate further undergo exchange reaction with other dichalcogenides in a one-pot operation. (C) 2014 Elsevier Ltd. All rights reserved.