O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose | 1350618-75-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(1R,2R,3S,4R,5R)-2,4-bis(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 1350618-75-5
• 化学式: C₃₄H₄₀O₁₄
• 分子量: 672.683
• InChiKey: IKQNTVTYXWPJOA-MKBWQVEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,6-anhydro-2,4-di-O-benzyl-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72%的产率得到O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-2,4-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
• 作为产物：
  描述：

  1,6-脱水-β-D-葡萄糖 在 silver trifluoromethanesulfonate 、 barium(II) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,6-anhydro-2,4-di-O-benzyl-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

• Stereoselective synthesis of α-glycosyl azides by ring-opening of 1,6-anhydrosugars with trimethylsilyl azide
  作者：Tianyu Cui、Raymond Smith、Xiangming Zhu

  DOI：10.1016/j.carres.2015.08.002

  日期：2015.10

  We describe here an expedient and highly stereoselective procedure for the synthesis of alpha-glycosyl azides. Treatment of 1,6-anhydrosugars with trimethylsilyl azide in the presence of trimethylsilyl triflate led to the formation of alpha-glycosyl azides. All the reactions were highly stereoselective and afforded the alpha-glycosyl azides in good to excellent yields.

  我们在这里描述了一种方便且高度立体选择性的合成α-糖基叠氮化物的方法。在三甲基甲硅烷基三氟甲磺酸酯存在下用三甲基甲硅烷基叠氮化物处理1，6-脱水糖导致形成α-糖基叠氮化物。所有反应都是高度立体选择性的，并以良好至优异的产率提供了α-糖基叠氮化物。