1,2:3,4-di-O-isopropylidene-6-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-dithio)-α-D-galactopyranoside | 1253890-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-dithio)-α-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(1S,2R,6R,8S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyldisulfanyl]oxan-2-yl]methyl acetate
• CAS: 1253890-58-2
• 化学式: C₂₆H₃₈O₁₄S₂
• 分子量: 638.711
• InChiKey: PLJBEPUWGMAIDC-GRHATEEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  211
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 在 silver(I) acetate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.84h， 生成 1,2:3,4-di-O-isopropylidene-6-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-dithio)-α-D-galactopyranoside
  参考文献：
  名称：

  Glycosylation via mixed disulfide formation using glycosylthio-phthalimides and -succinimides as glycosylsulfenyl-transfer reagents

  摘要：

  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.

  DOI：

  10.1016/j.carres.2011.04.020

文献信息

• A high-yielding, one-pot preparation of unsymmetrical glycosyl disulfides using 1-chlorobenzotriazole as an in situ trapping/oxidizing agent
  作者：Nashia Stellenboom、Roger Hunter、Mino R. Caira、László Szilágyi

  DOI：10.1016/j.tetlet.2010.07.176

  日期：2010.10

  A high-yielding, one-pot methodology for preparing unsymmetrical glycosyl disulfides derived from sugar, alkyl/aryl or cysteine thiols is reported using 1-chlorobenzotriazole (BtCl) as the oxidant. The highlight of the method is the low temperature of coupling (−78 °C) as well as the in situ trapping of the sulfenyl intermediate, which ensures that no homodimer of R1SH (R1SSR1) is formed. The coupling

  据报道，使用1-氯苯并三唑（BtCl）作为氧化剂，制备了一种高产率的一锅法方法，用于制备衍生自糖，烷基/芳基或半胱氨酸硫醇的不对称糖基二硫化物。该方法的亮点是偶联温度低（-78°C）以及亚磺基中间体的原位捕获，可确保不形成R 1 SH（R 1 SSR 1）的均二聚体。偶联效率与糖类型，糖中的硫醇位置，糖保护基团无关，并且各种产品用于说明糖生物学中许多模型系统的快速合成途径。