(2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-((4aR,6R,7R,8R,8aS)-6-benzyloxy-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 139534-89-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-((4aR,6R,7R,8R,8aS)-6-benzyloxy-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,4S,5R,6S)-2-[[(4aR,6R,7R,8R,8aS)-7-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-5-acetamido-4-benzoyloxy-6-[(1S,2R)-1,2,3-tribenzoyloxypropyl]oxane-2-carboxylate
• CAS: 139534-89-7
• 化学式: C₆₀H₅₇NO₁₈
• 分子量: 1080.11
• InChiKey: XWQMMDZIFOGEBO-CUPUSMOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  79.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  236.21
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  Benzyl 4,6-O-benzylidene-β-D-galactopyranoside 、 (2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-ethoxythiocarbonylsulfanyl-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 甲基硫基溴化物 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 二异丙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以17%的产率得到(4S,5R,6S)-5-Acetylamino-4-benzoyloxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Glycosylation with sialic acid at HO-3 of three different O-protected D-galactosides in acetonitrile/dichloromethane at low temperature

  摘要：

  Three different O-protected D-galactosides have been compared as acceptors in alpha-sialoside synthesis using glycosyl donor 1, methylsulfenyl triflate as promoter, and acetonitrile/dichloromethane as solvent at - 70-degrees-C. The 6-O-benzylated acceptor 2 was the most efficient, the alpha(2-3) sialoside 5 was obtained in 39% isolated yield.

  DOI：

  10.1016/0040-4039(91)80133-q