3,4,6-Tri-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-galactopyranosyl bromide | 151475-05-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-Tri-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-galactopyranosyl bromide
• 英文别名: [(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-bromooxan-3-yl] 4-cyanobenzoate
• CAS: 151475-05-7
• 化学式: C₂₀H₂₀BrNO₉
• 分子量: 498.284
• InChiKey: AUYFIYZYQLDRMB-SPOLIRPYSA-N

物化性质

• 沸点：
  566.3±50.0 °C(predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  138.22
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,4,6-Tri-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-galactopyranosyl bromide 在 四丁基溴化铵 、 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 29.0h， 生成 [(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-[(2R,3S,4S,5R,6R)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-methoxyoxan-4-yl]oxyoxan-3-yl] 4-cyanobenzoate
  参考文献：
  名称：

  Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter

  摘要：

  3,4,6-Tri-O-acetyl-1,2-O-(1-cyanobenzylidene)-alpha-D-galactopyranoses with differently substituted aromatic nuclei have been synthesised and used as glycosyl donors in reactions with the acceptors methyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-galactopyranoside (11) and methyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-D-galactopyranoside (12). The glycosylation of 11 gave only beta products. The efficiency and stereoselectivity of the glycosylations of 12 depend on the nature of the substituent in the aromatic ring. The stereoselectivity for the formation of 1,2-trans-glycosidic bonds was the highest with the p-methoxy-benzylidene derivative with triphenylmethylium triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80006-z
• 作为产物：
  描述：

  1,3,4,6-四-o-乙酰基-alpha-d-吡喃半乳糖 在 吡啶 、 乙酰溴 、 水 、 乙酸酐 、 溶剂黄146 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 2.0h， 生成 3,4,6-Tri-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-galactopyranosyl bromide
  参考文献：
  名称：

  Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter

  摘要：

  3,4,6-Tri-O-acetyl-1,2-O-(1-cyanobenzylidene)-alpha-D-galactopyranoses with differently substituted aromatic nuclei have been synthesised and used as glycosyl donors in reactions with the acceptors methyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-galactopyranoside (11) and methyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-D-galactopyranoside (12). The glycosylation of 11 gave only beta products. The efficiency and stereoselectivity of the glycosylations of 12 depend on the nature of the substituent in the aromatic ring. The stereoselectivity for the formation of 1,2-trans-glycosidic bonds was the highest with the p-methoxy-benzylidene derivative with triphenylmethylium triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80006-z