2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1,1')-dithio-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 1318853-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1,1')-dithio-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-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: 1318853-01-8
• 化学式: C₂₈H₃₈O₁₈S₂
• 分子量: 726.731
• InChiKey: CLMCVBFAPFXQDB-MSMUBDTHSA-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

• 作为产物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 、 N-phthalyl-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)sulfenamide 以 乙酸乙酯 为溶剂， 反应 2.0h， 以89%的产率得到2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1,1')-dithio-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  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