α-Selective Glycosidation of the Rare Sugar d-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide.

ABSTRACT: d-Tagatose is a rare sugar that exhibits intriguing biological properties, such as its role as a low-calorie sweetener and its ability to reduce the glycemic response. Consequently, the synthesis of d-tagatose derivatives is a crucial endeavor for the advancement of their functionalities, as well as elucidation of their biological properties. In this study, we present the α-selective glycosidation of a 1,3,4,6-tetra-O-benzoylated d-tagatofuranosyl donor with various glycosyl acceptors. In contrast to d-allulose, which is the C3,C4-epimer of d-tagatose and does not exhibit the neighboring group effect, the current d-tagatofuranosyl donor demonstrated significant neighboring group participation, achieving high α-selectivity ratios up to α:β = 99:1. This method was also applicable to t

SUBMITTER: Makura Y 

PROVIDER: S-EPMC12429656 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature