methyl (3aR,4R,6R,7aS)-3-acetyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-6-[[(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methoxy]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate | 1345019-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3aR,4R,6R,7aS)-3-acetyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-6-[[(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methoxy]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate
• CAS: 1345019-98-8
• 化学式: C₅₃H₅₃NO₂₀S
• 分子量: 1056.06
• InChiKey: SBOJECKDZCVMIX-MMASOIFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  75
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  284
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  methyl p-tolyl 5-acetamido 7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosonate 、 p-methylphenyl 2,3,4-tri-O-benzoyl-1-thio-β-galactopyranoside 在 4-甲基苯硫氯 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 以91%的产率得到methyl (3aR,4R,6R,7aS)-3-acetyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-6-[[(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methoxy]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate
  参考文献：
  名称：

  Pre-activation based, highly alpha-selective O-sialylation with N-acetyl-5-N,4-O-carbonyl-protected p-tolyl thiosialoside donor

  摘要：

  A new method for pre-activation of N-acetyl-5-N,4-O-carbonyl-protected p-tolyl thiosialoside donor with AgOTf and p-toluenesulfenyl chloride followed by coupling with other p-tolyl thioglycosides is reported. Excellent alpha-sialylation yields were achieved for these coupling reactions, as high as 91% yield of only alpha-isomer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.022