S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)disulfide | 356055-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)disulfide
• 英文别名: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1,1')-dithio-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]disulfanyl]oxan-2-yl]methyl acetate
• CAS: 356055-09-9
• 化学式: C₂₈H₃₈O₁₈S₂
• 分子量: 726.731
• InChiKey: CLMCVBFAPFXQDB-VCXZOCJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  280
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)disulfide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 D-Glcp-βS(1->1')Sβ-D-Galp
  参考文献：
  名称：

  新型糖苷间键的合成：二硫键二糖的合成

  摘要：

  通过使四乙酰基-β-d-吡喃葡萄糖基甲硫基磺酸盐与O-乙酰化的1-硫代-醛基吡喃糖反应，在温和条件下合成了具有糖苷间二硫键的不对称非还原性二糖。围绕SS键的优选构象与在无约束二硫键下（-90°）观察到的构象相近。

  DOI：

  10.1016/s0040-4039(01)00578-0
• 作为产物：
  描述：

  2-{1-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thio]-(1-methyl)ethyl}-malonic acid diethyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)disulfide
  参考文献：
  名称：

  通过亚磺酸有效合成不对称二硫化物

  摘要：

  不对称二硫化物，其中一些具有生物学意义，是通过从合适的亚磺酰基前体原位生成次磺酸并将其与各种硫醇偶联来制备的。这种方法代表了一种以极好的收率获得二硫化物的有效且温和的程序。在选择合适的次磺酸前体的基础上，它允许在次磺酸和硫醇中存在碱/酸和/或不耐热的官能团，并提供广泛的机会来调节不同结构骨架之间的二硫键的构建，例如作为同和杂芳族、氨基酸和糖残基。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900986

文献信息

• Glycosylation via mixed disulfide formation using glycosylthio-phthalimides and -succinimides as glycosylsulfenyl-transfer reagents
  作者：Tünde-Zita Illyés、Tamás Szabó、László Szilágyi

  DOI：10.1016/j.carres.2011.04.020

  日期：2011.9

  The silver salts of tetra-O-acetyl alpha- or -beta-D-glycopyranosyl thiols 1a-4a react smoothly with N-bromophthalimide and N-bromosuccinimide to furnish glycosylthio-phthalimide (1b-4b) and -succinimide (1c-3c) derivatives. Reactions of these reagents with aliphatic, aromatic, and glycosyl thiols as well as with cysteine and glutathione result in the formation of glycosylated mixed disulfides under mild conditions and in good yields. The S-glycosyl-N-acylsulfenamides described here represent novel, convenient glycosylsulfenyl-transfer reagents in effecting glycosylation of various thiols, including sugars, amino acids and peptides, through disulfide formation and can, therefore, be useful in controlled glycosylation of proteins as well. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.