methyl (3aR,4R,6R,7aS)-6-[[(2S,4aR,6S,7R,8R,8aR)-6-(4-methylphenyl)sulfanyl-2-phenyl-7-(2,2,2-trichloroethoxycarbonylamino)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3-acetyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate | 1345020-07-6

• 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-[[(2S,4aR,6S,7R,8R,8aR)-6-(4-methylphenyl)sulfanyl-2-phenyl-7-(2,2,2-trichloroethoxycarbonylamino)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-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: 1345020-07-6
• 化学式: C₄₂H₄₇Cl₃N₂O₁₈S
• 分子量: 1006.26
• InChiKey: RZXIXUXBVPFAEV-KHWQOWGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  66
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  262
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  p-tolyl 4,6-O-benzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-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78%的产率得到methyl (3aR,4R,6R,7aS)-6-[[(2S,4aR,6S,7R,8R,8aR)-6-(4-methylphenyl)sulfanyl-2-phenyl-7-(2,2,2-trichloroethoxycarbonylamino)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-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