2-methyl-4,5-(3,4-di-O-benzoyl-6-S-(4-methylphenyl)-6-thio-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline | 1159180-99-0

• 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-methyl-4,5-(3,4-di-O-benzoyl-6-S-(4-methylphenyl)-6-thio-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline
• 英文别名: [(3aR,5S,6S,7R,7aR)-7-benzoyloxy-2-methyl-5-[(4-methylphenyl)sulfanylmethyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-6-yl] benzoate
• CAS: 1159180-99-0
• 化学式: C₂₉H₂₇NO₆S
• 分子量: 517.602
• InChiKey: RZWXQWKJZWYIER-FSJVOCHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(2R,3S,4R,5R,6S)-5-acetamido-4-benzoyloxy-2-(hydroxymethyl)-6-(4-methylphenyl)sulfanyloxan-3-yl] benzoate 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到2-methyl-4,5-(3,4-di-O-benzoyl-6-S-(4-methylphenyl)-6-thio-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline
  参考文献：
  名称：

  DAST-Mediated Regioselective Anomeric Group Migration in Saccharides

  摘要：

  When saccharides bearing a sulfur, selenium, or oxygen substituent at the anomeric center and an unprotected hydroxyl group either at C-4 or C-6 were subjected to fluorination with DAST in dichloromethane, a regioselective migration of the anomeric substituent to the C-4 or C-6 position was observed. Certain saccharides gave a mixture of migration and normal fluorination products whereas others yielded mainly or exclusively migration products (beta-glycosyl fluorides). The high thermal and chemical stability of migrated glycosyl fluorides were demonstrated to be an important precursor for many significant carbohydrate analogies. It is therefore suggested that these migrations may have useful applications in organic synthesis.

  DOI：

  10.1021/jo900516r