A Facile and Efficient Method for the Synthesis of 1,2-Sugar Orthoesters

稿件作者:Shanqiao Wei
通讯作者:邵华武
刊物名称:第七届全国天然有机化学学术研讨会论文集,成都,2008年9月
发表年份:2008
卷:
期:
页码:127-127
影响因子:
文章摘要:
Sugar1,2-orthoesters are one of the most important intermediates in the organic synthesis and natural product synthesis ,[1,2] especially in the oligosaccharide synthesis .[3-5] Orthoesters typically undergo rearrangement by the action of protonic or Lewis acids ,resulting in the formation of glycosidic products .[6] These methods for the synthesis of sugar 1,2-sugar orthoesters involve the treatment of peracetylated glycosyl bromides with alcohols in the presence of a quaternary ammonium salt and 2,6-lutidine et al[7,8] Although the methods have been extensively used ,there is still a large disadvantage , the use of an organic base which is smelly ,toxic and eco-unfriendly . Herein in a facile and efficient method for synthesis of 1,2-orthoesters promoted by potassium fluoride instead of organic base was reported . Our goal is to establish the feasibility of this reaction as a general method for the synthesis of 1,2-orthoesters,[9] even sugar-sugar orthoesters . Various sugar orthoesters were prepared in good yield .
全文链接: