p-tolyl 6-O-acetyl-2-azido-2-deoxy-thio-1-β-D-glucopyranoside | 1262201-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 6-O-acetyl-2-azido-2-deoxy-thio-1-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methyl acetate
• CAS: 1262201-90-0
• 化学式: C₁₅H₁₉N₃O₅S
• 分子量: 353.399
• InChiKey: DMFIKMAVPLVRIA-RYPNDVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-tolyl 6-O-acetyl-2-azido-2-deoxy-thio-1-β-D-glucopyranoside 、 2,2,2-三氯乙酰胺苄酯 在 三氟甲磺酸 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到p-tolyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxythio-1-α-D-glucopyranoside
  参考文献：
  名称：

  A green and regioselective acetylation of thioglycoside with ethyl acetate

  摘要：

  Treatment of saccharidic polyols in ethyl acetate with catalytic sulfuric acid leads to the corresponding primary monoacetate derivatives in good yields. The transesterification was realized by simple stirring without rigorous exclusion of moisture or oxygen. Our protocol is applicable to the regioselective mono-acetylation of amino sugars having different substituents at the 2-positions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.135
• 作为产物：
  描述：

  乙酸乙酯 、 4-methylphenyl 2-azido-2-deoxy-1-thio-D-glucopyranoside 在 硫酸 作用下， 以 水 为溶剂， 反应 12.0h， 以95%的产率得到p-tolyl 6-O-acetyl-2-azido-2-deoxy-thio-1-β-D-glucopyranoside
  参考文献：
  名称：

  A green and regioselective acetylation of thioglycoside with ethyl acetate

  摘要：

  Treatment of saccharidic polyols in ethyl acetate with catalytic sulfuric acid leads to the corresponding primary monoacetate derivatives in good yields. The transesterification was realized by simple stirring without rigorous exclusion of moisture or oxygen. Our protocol is applicable to the regioselective mono-acetylation of amino sugars having different substituents at the 2-positions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.135