3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl bromide | 1352827-05-4

• 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: 3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl bromide
• 英文别名: [(2R,3R,4S,5R,6S)-3,4-dibenzoyloxy-6-bromo-5-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 1352827-05-4
• 化学式: C₃₄H₂₉BrO₈
• 分子量: 645.503
• InChiKey: MCWGFUOZSAXGGH-PXPWAULYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ethyl 2-O-benzyl-3,4,6-tri-O-benzoyl-1-thio-α-D-glucopyranoside 在 溴 作用下， 以 氘代氯仿 为溶剂， 生成 3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl bromide
  参考文献：
  名称：

  Glycosidation of Thioglycosides in the Presence of Bromine: Mechanism, Reactivity, and Stereoselectivity

  摘要：

  Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that beta-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, alpha-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into alpha-bromide that is totally unreactive under the established reaction conditions.

  DOI：

  10.1021/jo2019174

文献信息

• Glycosidation of Thioglycosides in the Presence of Bromine: Mechanism, Reactivity, and Stereoselectivity
  作者：Sophon Kaeothip、Jagodige P. Yasomanee、Alexei V. Demchenko

  DOI：10.1021/jo2019174

  日期：2012.1.6

  Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that beta-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, alpha-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into alpha-bromide that is totally unreactive under the established reaction conditions.