Stereocontrolled synthesis of α-d-allulofuranosides using α-selective d-fructofuranosidation reaction

Carbohydr Res. 2024 Jan 30;536:109044. doi: 10.1016/j.carres.2024.109044. Online ahead of print.ABSTRACTStereocontrolled synthesis of rare sugar derivatives, namely α-d-allulofuranosides, was achieved using d-fructose, one of the most abundant carbohydrates in nature. The following are the key steps of the α-d-allulofuranosides' synthesis. (1) An α-selective glycosidation reaction of 1,3,4,6-tetra-O-benzoylated d-fructofuranosyl donor to obtain α-d-fructofuranosides with 98 %-75 % isolated yields. (2) A regioselective 1,4,6-tri-O-pivaloylation reaction of the tetraol of α-d-fructofuranosides with the C3-hydroxy group remaining intact. (3) The oxidation of the C3-hydroxy group followed by the stereoselective reduction of the C3-carbonyl group. Primary and secondary alcohols and sugars can be used as glycosyl acceptors and aglycones for the following pivaloylation and stereoinversion reactions to obtain α-d-allulofuranosides.PMID:38325068 | DOI:10.1016/j.carres.2024.109044
Source: Carbohydrate Research - Category: Genetics & Stem Cells Authors: Source Type: research