1,3,4,6-Tetra-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-glucopyranose | 151475-03-5

• 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: 1,3,4,6-Tetra-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-2,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-3-yl] 4-cyanobenzoate
• CAS: 151475-03-5
• 化学式: C₂₂H₂₃NO₁₁
• 分子量: 477.425
• InChiKey: DMRHEXRDWMBXBF-QWPXSNKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  164.52
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,3,4,6-Tetra-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-glucopyranose 在 乙酰溴 、 水 、 乙酸酐 、 溶剂黄146 作用下， 以 氯仿 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
• 作为产物：
  描述：

  对氰基苯甲酰氯 、 1,3,4,6-四-o-乙酰基-alpha-d-吡喃半乳糖 在 吡啶 作用下， 以 乙腈 为溶剂， 以90%的产率得到1,3,4,6-Tetra-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-glucopyranose
  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