2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-glucopyranose | 1350618-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)-2-sulfanyloxan-3-yl] benzoate
• CAS: 1350618-88-0
• 化学式: C₂₇H₂₈O₆S
• 分子量: 480.582
• InChiKey: PVOCSKRQNIOYRO-ZANOAUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,6-酸酐-2,3,4-三-O-苄基-β-D-吡喃葡萄糖 在 吡啶 、 双(三甲基硫化硅) 、 三氟甲磺酸三甲基硅酯 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成 2-O-benzoyl-3,4-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

文献信息

• Synthesis of α-Glycosyl Thiols by Stereospecific Ring-Opening of 1,6-Anhydrosugars
  作者：Xiangming Zhu、Ravindra T. Dere、Junyan Jiang、Lei Zhang、Xiaoxia Wang

  DOI：10.1021/jo202069y

  日期：2011.12.16

  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.