methyl 6-O-acetyl-3,4-O-isopropylidene-5-C-methoxy-β-D-lyxo-hexopyranosid-2-ulose | 259751-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-acetyl-3,4-O-isopropylidene-5-C-methoxy-β-D-lyxo-hexopyranosid-2-ulose
• CAS: 259751-59-2
• 化学式: C₁₃H₂₀O₈
• 分子量: 304.297
• InChiKey: SMXCQTVOFXORJW-PRULPYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-acetyl-3,4-O-isopropylidene-5-C-methoxy-β-D-lyxo-hexopyranosid-2-ulose 在 sodium tetrahydroborate 、 Amberlist 15 ion-exchange resin 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 29.0h， 生成 methyl 2,3,4,6-tetra-O-acetyl-5-C-methoxy-β-D-talopyranoside
  参考文献：
  名称：

  The First Synthesis of aRibo-Hexos-5-Ulose: the L-Enantiomer

  摘要：

  The title compound, previously unreported in either enantioform, and its 2,6-di-O-benzyl derivative have been synthesized through a stereocontrolled epimerization at C-2 of 6-O-protected methyl 3,4-O-isopropylidene-5-C-methoxy-beta-D-galactopyranosides The epimerization, performed through a high yielding sequence of oxidation-reduction owing to the cooperative role of the equatorial C-l aglycon and the steric hindrance of the isopropylidene group, turned out to be completely diastereoselective. Whereas the unprotected L-ribo-hexos-5-ulose exists, as proved by NMR in D2O, in five main tautomeric forms in a ratio of about 4:2:2:1:1, only two anomeric 1,4-furanosic forms are present at equilibrium in its 2,6-di-O-benzyl derivative, in ratios ranging from 10:1 to 7:3, depending on the prevalence of D2O or CD3CN in the solvent mixture.

  DOI：

  10.1080/07328309908544053
• 作为产物：
  描述：

  methyl 6-O-acetyl-3,4-O-isopropylidene-5-C-methoxy-β-D-galactopyranoside 在 N-甲基吲哚酮 、 molecular sieve 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以576 mg的产率得到methyl 6-O-acetyl-3,4-O-isopropylidene-5-C-methoxy-β-D-lyxo-hexopyranosid-2-ulose
  参考文献：
  名称：

  The First Synthesis of aRibo-Hexos-5-Ulose: the L-Enantiomer

  摘要：

  The title compound, previously unreported in either enantioform, and its 2,6-di-O-benzyl derivative have been synthesized through a stereocontrolled epimerization at C-2 of 6-O-protected methyl 3,4-O-isopropylidene-5-C-methoxy-beta-D-galactopyranosides The epimerization, performed through a high yielding sequence of oxidation-reduction owing to the cooperative role of the equatorial C-l aglycon and the steric hindrance of the isopropylidene group, turned out to be completely diastereoselective. Whereas the unprotected L-ribo-hexos-5-ulose exists, as proved by NMR in D2O, in five main tautomeric forms in a ratio of about 4:2:2:1:1, only two anomeric 1,4-furanosic forms are present at equilibrium in its 2,6-di-O-benzyl derivative, in ratios ranging from 10:1 to 7:3, depending on the prevalence of D2O or CD3CN in the solvent mixture.

  DOI：

  10.1080/07328309908544053