ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) disulfide | 231607-35-5

• 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: ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) disulfide
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(ethyldisulfanyl)oxan-2-yl]methyl acetate
• CAS: 231607-35-5
• 化学式: C₁₆H₂₄O₉S₂
• 分子量: 424.493
• InChiKey: QMGVROKGZJDDRR-LJIZCISZSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  482.6±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) disulfide 在 一溴化碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物
  参考文献：
  名称：

  糖基二硫化物：一类新的溶液和固相糖基供体

  摘要：

  混合糖基二硫化物不仅是糖模拟物，而且是糖基供体，可以很容易地以武装醚保护或解除武装酯保护的形式构建，并以相应的糖基甲硫代磺酸盐以可溶或固体支持的形式构建，并用于各种代表性受体的糖基化.

  DOI：

  10.1039/b008734n
• 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， 生成 ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) disulfide
  参考文献：
  名称：

  Glyco-SeS：亚硒硫醚介导的蛋白质糖缀合——一种翻译后修饰的新策略。

  摘要：

  DOI：

  10.1002/anie.200352975

文献信息

• Glycosyl phenylthiosulfonates (Glyco-PTS): novel reagents for glycoprotein synthesisThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.Electronic supplementary information (ESI) available: experimental procedures, characterization, protein ESI-MS spectra and crystal data. See http://www.rsc.org/suppdata/ob/b3/b306990g/
  作者：David P. Gamblin、Philippe Garnier、Sarah J. Ward、Neil J. Oldham、Antony J. Fairbanks、Benjamin G. Davis

  DOI：10.1039/b306990g

  日期：——

  Controlled site-selective glycosylation can be achieved by combining site-directed cysteine mutagenesis with chemical modification of the introduced thiol; a new class of more efficient chemoselective reagents, glycosyl phenylthiosulfonates, allow rapid glycosylations of representative simple thiols, peptides and proteins.

  通过将定点半胱氨酸诱变与引入的硫醇的化学修饰相结合，可以实现受控的位点选择性糖基化。新型的更有效的化学选择试剂，糖基苯基硫代磺酸盐，可以使代表性的简单硫醇，肽和蛋白质快速糖基化。
• Direct Synthesis of Unsymmetrical Glycosyl Disulfides from Glycosyl Bromides
  作者：Monalisa Kundu、Anup Kumar Misra

  DOI：10.1002/ejoc.202100606

  日期：2021.7.15

  A fast one step reaction condition has been developed for the synthesis of unsymmetrical anomeric glycosyl disulfide derivatives from anomeric glycosyl bromides in excellent yield.

  已经开发了一种快速一步反应条件，用于从异头糖基溴化物以优异的收率合成不对称异头糖基二硫化物衍生物。
• Glycosyl Disulfides:  Novel Glycosylating Reagents with Flexible Aglycon Alteration
  作者：Elizabeth J. Grayson、Sarah J. Ward、Alison L. Hall、Phillip M. Rendle、David P. Gamblin、Andrei S. Batsanov、Benjamin G. Davis

  DOI：10.1021/jo051374j

  日期：2005.11.1

  Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning Strategies,.
• [EN] REAGENTS AND METHODS FOR THE FORMATION OF DISULFIDE BONDS AND THE GLYCOSYLATION OF PROTEINS<br/>[FR] REACTIFS ET PROCEDES POUR FORMER DES LIAISONS DISULFURE ET POUR GLYCOSYLER DES PROTEINES
  申请人：ISIS INNOVATION

  公开号：WO2005000862A3

  公开（公告）日：2005-08-18
• Efficient one-pot synthesis of glycosyl disulfides
  作者：Goreti Ribeiro Morais、Robert A. Falconer

  DOI：10.1016/j.tetlet.2007.08.106

  日期：2007.10

  Methodology for the efficient and facile synthesis of glycosyl disulfides is reported. A one-pot procedure employing mild conditions using diethyl azodicarboxylate is described to synthesise a series of glycosyl disulfides in excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.