2,6-dideoxy-3,4-di-O-benzyl-2-N-phthalimido-6-S-(4-methylphenyl)-6-thio-β-D-glucopyranosyl fluoride | 1159181-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,6-dideoxy-3,4-di-O-benzyl-2-N-phthalimido-6-S-(4-methylphenyl)-6-thio-β-D-glucopyranosyl fluoride
• 英文别名: 2-[(2S,3R,4R,5S,6S)-2-fluoro-6-[(4-methylphenyl)sulfanylmethyl]-4,5-bis(phenylmethoxy)oxan-3-yl]isoindole-1,3-dione
• CAS: 1159181-22-2
• 化学式: C₃₅H₃₂FNO₅S
• 分子量: 597.707
• InChiKey: QEUKMBWOPFMCAE-YKNMHBIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-[(2S,3R,4R,5S,6R)-6-(hydroxymethyl)-2-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxan-3-yl]isoindole-1,3-dione 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70%的产率得到2,6-dideoxy-3,4-di-O-benzyl-2-N-phthalimido-6-S-(4-methylphenyl)-6-thio-β-D-glucopyranosyl fluoride
  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