Benzyl 2,3,6,2',3',4',6'-hepta-O-acetyl-α-lactoside | 67310-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 2,3,6,2',3',4',6'-hepta-O-acetyl-α-lactoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-phenylmethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 67310-52-5
• 化学式: C₃₃H₄₂O₁₈
• 分子量: 726.686
• InChiKey: BDMTWMBGISDBOQ-WPHPRKDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  Benzyl 2,3,6,2',3',4',6'-hepta-O-acetyl-α-lactoside 在 palladium on activated charcoal 甲酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 4’-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2’,3’,6’-tri-O-acetyl-D-glucopyranose 、 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and characterization of 6-O-β-lactosyl-α,β-d-mannopyranoses and 2,6-di-O-β-lactosyl-α,β-d-manno-pyranoses

  摘要：

  The reaction of 2,3,6,2',3',4',6'-hepta-O-acetyl-alpha-lactosyl bromide (4) and benzyl 3,4-di-O-benzyl-alpha-D-mannopyranoside (3) in the presence of mercury(II) cyanide in benzene-nitromethane produced benzyl 3,4-di-O-benzyl-2,6-bis-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-beta-lactosyl)-alpha-D-mannopyranoside (5) and benzyl 3,4-di-O-benzyl-6-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-beta-lactosyl)-alpha-D-mannopyranoside (6), as part of a complex mixture. Column chromatography, followed by acetylation of the fraction containing 5 and 6, gave a sample of 5 and benzyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-beta-lactosyl)-alpha-D-mannopyranoside (7) in approximately 35% and 17% yields (based on 4), respectively. Deprotection of 5 and 7 afforded the target compounds, namely 2,6-di-O-beta-lactosyl-alpha,beta-D-mannopyranoses and 6-O-beta-lactosyl-alpha,beta-D-mannopyranoses, respectively. If the coupling of 4 with 3 were performed in the presence of silver trifluoromethanesulfonate and 2,4,6-trimethylpyridine, only a mixture of 3,6,2',3',4',6'-hexa-O-acetyl-alpha-lactose-1,2-{[3,6, 2',3',4',6'-hexa-O-acetyl-alpha-lactose 1,2-(benzyl 3,4-di-O-benzyl-alpha-D-mannopyranosid-6-yl orthoacetyl)-2-yl] orthoacetate} and 3,6,2',3',4',6'-hexa-O-acetyl-alpha-lactose 1,2-(benzyl 3,4-di-O-benzyl-alpha-D-mannopyranosid-6-yl orthoacetate) was obtained. The orthoacetates were characterized by n.m.r. spectroscopy. The two target materials are useful in the assessment of the binding properties of galactose-terminated ligands to the asialoglycoprotein receptor of normal rabbit and human hepatocytes.

  DOI：

  10.1016/0008-6215(91)89042-e
• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 2,4,6-三甲基吡啶 、 甲酸 、 四丁基溴化铵 、 silver(l) oxide 作用下， 反应 17.75h， 生成 Benzyl 2,3,6,2',3',4',6'-hepta-O-acetyl-α-lactoside
  参考文献：
  名称：

  Synthesis and characterization of 6-O-β-lactosyl-α,β-d-mannopyranoses and 2,6-di-O-β-lactosyl-α,β-d-manno-pyranoses

  摘要：

  The reaction of 2,3,6,2',3',4',6'-hepta-O-acetyl-alpha-lactosyl bromide (4) and benzyl 3,4-di-O-benzyl-alpha-D-mannopyranoside (3) in the presence of mercury(II) cyanide in benzene-nitromethane produced benzyl 3,4-di-O-benzyl-2,6-bis-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-beta-lactosyl)-alpha-D-mannopyranoside (5) and benzyl 3,4-di-O-benzyl-6-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-beta-lactosyl)-alpha-D-mannopyranoside (6), as part of a complex mixture. Column chromatography, followed by acetylation of the fraction containing 5 and 6, gave a sample of 5 and benzyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-beta-lactosyl)-alpha-D-mannopyranoside (7) in approximately 35% and 17% yields (based on 4), respectively. Deprotection of 5 and 7 afforded the target compounds, namely 2,6-di-O-beta-lactosyl-alpha,beta-D-mannopyranoses and 6-O-beta-lactosyl-alpha,beta-D-mannopyranoses, respectively. If the coupling of 4 with 3 were performed in the presence of silver trifluoromethanesulfonate and 2,4,6-trimethylpyridine, only a mixture of 3,6,2',3',4',6'-hexa-O-acetyl-alpha-lactose-1,2-{[3,6, 2',3',4',6'-hexa-O-acetyl-alpha-lactose 1,2-(benzyl 3,4-di-O-benzyl-alpha-D-mannopyranosid-6-yl orthoacetyl)-2-yl] orthoacetate} and 3,6,2',3',4',6'-hexa-O-acetyl-alpha-lactose 1,2-(benzyl 3,4-di-O-benzyl-alpha-D-mannopyranosid-6-yl orthoacetate) was obtained. The orthoacetates were characterized by n.m.r. spectroscopy. The two target materials are useful in the assessment of the binding properties of galactose-terminated ligands to the asialoglycoprotein receptor of normal rabbit and human hepatocytes.

  DOI：

  10.1016/0008-6215(91)89042-e