2,3,4,-tri-O-allyl-1-thio-α-D-glucopyranose | 1042397-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,-tri-O-allyl-1-thio-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tris(prop-2-enoxy)-6-sulfanyloxan-2-yl]methanol
• CAS: 1042397-92-1
• 化学式: C₁₅H₂₄O₅S
• 分子量: 316.419
• InChiKey: MPVCLVSNRXPWLM-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,6-anhydro-2,3,4-tri-O-allyl-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78%的产率得到2,3,4,-tri-O-allyl-1-thio-α-D-glucopyranose
  参考文献：
  名称：

  A direct and stereospecific approach to the synthesis of α-glycosyl thiols

  摘要：

  本文介绍了一种合成δ-糖基硫醇的新的简单方法。在催化剂 TMSOTf 的作用下，1,6-酸酐糖与市售的双(三甲基硅)硫化物开环，以非常高的产率和立体特异性的方式顺利得到了δ-糖基硫醇。

  DOI：

  10.1039/b804536d

文献信息

• Alpha-GLYCOSYL THIOLS AND alpha-S-LINKED GLYCOLIPIDS
  申请人：Zhu Xiangming

  公开号：US20100184711A1

  公开（公告）日：2010-07-22

  The present invention relates to stereoselective methods for the preparation of α-glycosyl thiols and α-S-linked glycosylceramides.

  本发明涉及用于制备α-糖基硫醇和α-S-链接糖基酰胺的立体选择性方法。
• 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.