1,6-anhydro-3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranose | 1350618-71-1

• 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: 1,6-anhydro-3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranose
• 英文别名: [(1R,2R,3S,4R,5R)-2,3-bis(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl] 2,2-dimethylpropanoate
• CAS: 1350618-71-1
• 化学式: C₂₅H₃₀O₆
• 分子量: 426.51
• InChiKey: CSSWIEFBYYHPGH-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3,4-di-O-benzyl-2-O-pivaloyl-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83%的产率得到3,4-di-O-benzyl-2-O-pivaloyl-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-酸酐-2,3,4-三-O-苄基-β-D-吡喃葡萄糖 在 吡啶 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成 1,6-anhydro-3,4-di-O-benzyl-2-O-pivaloyl-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

文献信息

• Glycosyl Dioxalenium Ions as Reactive Intermediates of Automated Electrochemical Assembly
  作者：Akito Shibuya、Moeko Kato、Asuka Saito、Sujit Manmode、Naoto Nishikori、Toshiyuki Itoh、Aiichiro Nagaki、Toshiki Nokami

  DOI：10.1002/ejoc.202200135

  日期：2022.5.19

  Glycosyl dioxalenium ions generated from thioglycosides were used as observable reaction intermediates for automated electrochemical assembly of β-1,6-glucans. VT-NMR measurement revealed thermal stability of glycosyl dioxalenium ions and reaction temperature was rationally optimized based on information of their stability.

  由硫糖苷产生的糖基二氧杂二硫鎓离子被用作可观察到的反应中间体，用于 β-1,6-葡聚糖的自动电化学组装。VT-NMR测量揭示了糖基二氧戊二烯离子的热稳定性，并且基于它们的稳定性信息合理地优化了反应温度。