methyl (3aR,4R,6R,7aS)-6-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-6-(4-methylphenyl)sulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy]-3-acetyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate | 1345020-08-7

• 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)-6-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-6-(4-methylphenyl)sulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy]-3-acetyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate
• CAS: 1345020-08-7
• 化学式: C₃₅H₄₅NO₁₇S
• 分子量: 783.805
• InChiKey: JWFMSWYBOFWUQM-UKAWVYSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  244
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  4-tolyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 、 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 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89%的产率得到methyl (3aR,4R,6R,7aS)-6-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-6-(4-methylphenyl)sulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy]-3-acetyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-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