methyl 2,3-di-O-allyl-4-O-benzyl-α-D-glucopyranoside | 58341-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-allyl-4-O-benzyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-6-methoxy-3-phenylmethoxy-4,5-bis(prop-2-enoxy)oxan-2-yl]methanol
• CAS: 58341-70-1
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: TULREUQXQSEDIP-OBKDMQGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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

• Glycosylation via Cp₂ZrCl₂/AgClO₄-Mediated Activation of Anomeric Sulfoxides
  作者：Peter Wipf、Jonathan T. Reeves

  DOI：10.1021/jo015952h

  日期：2001.11.1
• 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.