(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 1352278-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1352278-39-7
• 化学式: C₄₈H₄₆O₁₉
• 分子量: 926.882
• InChiKey: DQEXWDHPROVRFV-IXZUZDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  67
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  1,2-O-(α-methoxybenzylidene)-3,4,6-tri-O-benzoyl-β-D-mannopyranose 、 2,3,4,6-O-四乙酰基-D-吡喃甘露糖 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以38%的产率得到(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-benzoyl-β-D-mannopyranoside
  参考文献：
  名称：

  Unexpected Stereocontrolled Access to 1α,1′β-Disaccharides from Methyl 1,2-Ortho Esters

  摘要：

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1 alpha,1'beta-disaccharides, upon treatment with BF3 center dot Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.

  DOI：

  10.1021/jo202335n

文献信息

• Unexpected Stereocontrolled Access to 1α,1′β-Disaccharides from Methyl 1,2-Ortho Esters
  作者：Clara Uriel、Juan Ventura、Ana M. Gómez、J. Cristóbal López、Bert Fraser-Reid

  DOI：10.1021/jo202335n

  日期：2012.1.6

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1 alpha,1'beta-disaccharides, upon treatment with BF3 center dot Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.