p-cresyl 2,3,5-tri-O-acetyl-1-thio-α-D-[U-13C5]-arabinofuranoside | 219627-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-cresyl 2,3,5-tri-O-acetyl-1-thio-α-D-[U-13C5]-arabinofuranoside
• 英文别名: [(2R,3R,4S,5R)-3,4-diacetyloxy-5-(4-methylphenyl)sulfanyl(2,3,4,5-13C4)oxolan-2-yl](113C)methyl acetate
• CAS: 219627-30-2
• 化学式: C₁₈H₂₂O₇S
• 分子量: 387.379
• InChiKey: ZGLXRGOLHXAWPQ-ZPGBNRSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-cresyl 2,3,5-tri-O-acetyl-1-thio-α-D-[U-13C5]-arabinofuranoside 在 N-碘代丁二酰亚胺 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl [U-13C5]-arabinofuranosyl-(1->5)-α-D-arabinofuranoside
  参考文献：
  名称：

  Conversion of Pyranose Glycals to Furanose Derivatives:  A New Route to Oligofuranosides

  摘要：

  Acetylated pyranose glycals have been converted through a convenient three-step process into protected furanose reducing sugars. Ozonolysis of 2,3,5-tri-O-acetyl-glucal or 2,3,5-tri-O-acetyl-galactal, followed by treatment with dimethyl sulfide and then hydrolysis gave respectively protected arabinofuranose (6) and lyxofuranose (7) derivatives. Conversion of these hemiacetals to oligosaccharides was explored using a number of methods. Activation of 6 or 7 in situ afforded glycosides in modest yield and stereoselectivity. Glycosylation of tetraacetates 16 and 18, obtained from 6 and 7, gave similar results. However, thioglycosides 17 and 19, also derived from 6 and 7, were found to be effective glycosyl donors, producing products in good to excellent yields and with high stereoselectivities. The method was also used to synthesize a disaccharide in which one residue contained uniform C-13 enrichment.

  DOI：

  10.1021/jo9815406
• 作为产物：
  描述：

  [(2R,3R,4S,5S)-3,4-diacetyloxy-5-hydroxy(2,3,4,5-13C4)oxolan-2-yl](113C)methyl acetate 在 硫酸 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 p-cresyl 2,3,5-tri-O-acetyl-1-thio-α-D-[U-13C5]-arabinofuranoside
  参考文献：
  名称：

  Conversion of Pyranose Glycals to Furanose Derivatives:  A New Route to Oligofuranosides

  摘要：

  Acetylated pyranose glycals have been converted through a convenient three-step process into protected furanose reducing sugars. Ozonolysis of 2,3,5-tri-O-acetyl-glucal or 2,3,5-tri-O-acetyl-galactal, followed by treatment with dimethyl sulfide and then hydrolysis gave respectively protected arabinofuranose (6) and lyxofuranose (7) derivatives. Conversion of these hemiacetals to oligosaccharides was explored using a number of methods. Activation of 6 or 7 in situ afforded glycosides in modest yield and stereoselectivity. Glycosylation of tetraacetates 16 and 18, obtained from 6 and 7, gave similar results. However, thioglycosides 17 and 19, also derived from 6 and 7, were found to be effective glycosyl donors, producing products in good to excellent yields and with high stereoselectivities. The method was also used to synthesize a disaccharide in which one residue contained uniform C-13 enrichment.

  DOI：

  10.1021/jo9815406