A new, lipophilic p-alkoxybenzyl ether protecting group and its use in the synthesis of a disaccharide.
[formula: see text] In contrast to major advances in the chemical synthesis of oligosaccharides, the methods of purification of the intermediates are essentially the same as they were decades ago. Here, the synthesis of p-(dodecyloxy)benzyl chloride is described and it is demonstrated that the new p-(dodecyloxy)benzyl ether protecting group can render a protected disaccharide sufficiently lipophilic for selective adsorption on C18 silica, thus sidestepping the expensive silica gel chromatography traditionally used for the isolation of protected oligosaccharides.
Pozsgay
V
V
National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, Maryland 20892-2720, USA. vipo@helix.nih.gov
D001593:Benzyl Compounds / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002850:Chromatography, Gel; D004187:Disaccharides / Q000138:chemical synthesis*; D004987:Ethers / Q000737:chemistry*
D001593:Benzyl Compounds; D004187:Disaccharides; D004987:Ethers; C410135:p-(dodecyloxy)benzyl ether