benzyl 2,6-dideoxy-3-C-methyl-α-L-lyxo-hexopyranoside | 1133162-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,6-dideoxy-3-C-methyl-α-L-lyxo-hexopyranoside
• 英文别名: (2S,3R,4S,6R)-2,4-dimethyl-6-phenylmethoxyoxane-3,4-diol
• CAS: 1133162-61-4
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: QLYKPCJZTWYBKI-ASEORRQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  benzyl 2,6-dideoxy-4-O-(p-methoxybenzyl)-3-C-methyl-α-L-lyxo-hexopyranoside 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以37%的产率得到benzyl 2,6-dideoxy-3-C-methyl-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides

  摘要：

  We describe here the first use of 2,3-anhydrosugars as glycosylating agents for the preparation of 2-deoxypyranosides. In particular, the methodology was used to assemble 2,6-dideoxysugar glycosides. Glycosylation of a panel of alcohols with one of two 6-deoxy-2,3-anhydrosugar thioglycosides (8 and 9) in the presence of a Lewis acid afforded 2,6-dideoxy-2-thiotolyl glycoside products in generally excellent yields with an exclusively syn relationship between the aglycon and the C-3 hydroxyl group. Removal of the 2-thiotolyl group can be achieved upon reaction with tri-n-butyltin hydride and AIBN to give the corresponding 2,6-dideoxy pyranosides. Once developed, the method was applied to the synthesis of oligosaccharide moieties in the natural products apoptolidin and olivomycin A.

  DOI：

  10.1021/jo900131a