O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose | 1350618-77-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-[[(1R,2R,3S,4R,5R)-2,4-bis(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy]-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1350618-77-7
• 化学式: C₄₆H₅₆O₂₂
• 分子量: 960.937
• InChiKey: XCNQIXWREHWARU-ZJKPIDDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  68
• 可旋转键数：
  26
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  258
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose 在 双(三甲基硫化硅) 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of α-Glycosyl Thiols by Stereospecific Ring-Opening of 1,6-Anhydrosugars

  摘要：

  Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of a-glycosyl thiols. All the reactions were highly stereoselective and afforded the a-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding a-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to a-glycosyl thiols of great value was established.

  DOI：

  10.1021/jo202069y
• 作为产物：
  描述：

  1,6-脱水-β-D-葡萄糖 在 silver trifluoromethanesulfonate 、 barium(II) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of α-Glycosyl Thiols by Stereospecific Ring-Opening of 1,6-Anhydrosugars

  摘要：

  Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of a-glycosyl thiols. All the reactions were highly stereoselective and afforded the a-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding a-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to a-glycosyl thiols of great value was established.

  DOI：

  10.1021/jo202069y