(2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-((2R,3R,4S,5S,6R)-3-benzoyloxy-6-benzoyloxymethyl-2-benzyloxy-5-hydroxy-tetrahydro-pyran-4-yloxy)-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 139534-88-6

• 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-((2R,3R,4S,5S,6R)-3-benzoyloxy-6-benzoyloxymethyl-2-benzyloxy-5-hydroxy-tetrahydro-pyran-4-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)-5-acetamido-4-benzoyloxy-2-[(2R,3S,4S,5R,6R)-5-benzoyloxy-2-(benzoyloxymethyl)-3-hydroxy-6-phenylmethoxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-tribenzoyloxypropyl]oxane-2-carboxylate
• CAS: 139534-88-6
• 化学式: C₆₇H₆₁NO₂₀
• 分子量: 1200.22
• InChiKey: BVYXXRJPKYPWJH-BMQPZNHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  88
• 可旋转键数：
  30
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  270
• 氢给体数：
  2
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-5-benzoyloxy-3,4-dihydroxy-6-phenylmethoxyoxan-2-yl]methyl benzoate 、 (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31%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