Efficient Preparation of 2‐SAc‐Glycosyl Donors and Investigation of Their Application in the Synthesis of 2‐Deoxyglycosides

In this study, we have developed efficient strategies for the synthesis of glycosyl donors with 2‐thioacetyl (SAc) groups in order to synthesize 2‐deoxysugars with exclusive α/β‐configuration. Starting from free methyl glycosides, four methyl 2‐SAc glycosides were synthesized with high efficiency mainly through the double serial inversion strategy, and further turned into four corresponding 1‐OAc, 2‐SAc α‐glycosyl donors (manno‐, gluco‐, galacto‐ and talo‐types) and four corresponding 1‐STol, 2‐SAc 1,2‐cis‐glycosyl donors (manno‐, gluco‐, galacto‐ and talo‐types). Glycosylation of the 1‐OAc, 2‐SAc donors and further 2‐deoxysugar synthesis have also been investigated in this study. We have developed efficient strategies for the synthesis of glycosyl donors with 2‐thioacetyl (SAc) groups in order to synthesize 2‐deoxysugars with absolute α/β configuration.