6-O-benzoyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl bromide | 35094-62-3

• 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: 6-O-benzoyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl bromide
• CAS: 35094-62-3
• 化学式: C₃₄H₃₃BrO₆
• 分子量: 617.536
• InChiKey: MFYIPSZOGWEAJN-AALIFHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 6-O-benzoyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl bromide 在 四丁基溴化铵 作用下， 以 1,2-二氯乙烷 为溶剂， 以45%的产率得到methyl 6-O-benzoyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以59%的产率得到6-O-benzoyl-2,3,4-tri-O-benzyl-α-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