2,3-di-O-allyl-4-O-benzyl-1-thio-α-D-glucopyranose | 1042397-94-3

• 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: 2,3-di-O-allyl-4-O-benzyl-1-thio-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6R)-3-phenylmethoxy-4,5-bis(prop-2-enoxy)-6-sulfanyloxan-2-yl]methanol
• CAS: 1042397-94-3
• 化学式: C₁₉H₂₆O₅S
• 分子量: 366.478
• InChiKey: CDLOVCVSBDRBJG-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  methyl 2,3-di-O-allyl-4-O-benzyl-α-D-glucopyranoside 在 双(三甲基硫化硅) 、 三氟甲磺酸三甲基硅酯 、 iron perchlorate hexahydrate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 2,3-di-O-allyl-4-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

• 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。
• A direct and stereospecific approach to the synthesis of α-glycosyl thiols
  作者：Ravindra T. Dere、Yingxi Wang、Xiangming Zhu

  DOI：10.1039/b804536d

  日期：——

  A new simple method for the synthesis of α-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded α-glycosyl thiols in very high yields and in a stereospecific way.

  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。