methyl 2,3,5-tri-O-acetyl-α-D-lyxofuranoside | 110415-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,5-tri-O-acetyl-α-D-lyxofuranoside
• 英文别名: [(2R,3S,4S,5S)-3,4-diacetyloxy-5-methoxyoxolan-2-yl]methyl acetate
• CAS: 110415-60-6
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: RUSRQHXGPHZZNI-RHYQMDGZSA-N

物化性质

• 沸点：
  355.4±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  β-D-Ribofuranose-1,2,3,5-tetraacetate 在 N-碘代丁二酰亚胺 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.25h， 生成 methyl 2,3,5-tri-O-acetyl-α-D-lyxofuranoside
  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

文献信息

• Dahlhoff, Wilhelm V.; Fenzl, Wolfgang; Koester, Roland, Liebigs Annalen der Chemie, 1990, # 8, p. 807 - 810
  作者：Dahlhoff, Wilhelm V.、Fenzl, Wolfgang、Koester, Roland

  DOI：——

  日期：——
• DAHLHOFF, WILHELM V.;FENZL, WOLFGANG;KOSTER, ROLAND, LIEBIGS ANN. CHEM. ,(1990) N, C. 807-810
  作者：DAHLHOFF, WILHELM V.、FENZL, WOLFGANG、KOSTER, ROLAND

  DOI：——

  日期：——