One-pot synthesis of carbohydrate thionolactones from 1-thiosugars

Glycosyl disulfides: importance, synthesis and application to chemical and biological systems

“…54 Direct synthesis of the more stable glycosyl thiosulfinate from thiosugars, rather than oxi-dation of the glycosyl disulfide, partially overcomes this problem. 93…”

Glucose-based spiro-oxathiazoles as in vivo anti-hyperglycemic agents through glycogen phosphorylase inhibition

“…Based on this 1,3-dipolar cycloaddition analogy, the known Dglucono--thionolactone 12 [43][44][45] Please do not adjust margins Please do not adjust margins Following Fairbanks' procedure, thermal elimination was carried out in refluxing toluene with either the crude thiosulfinate 10 (two-step one-pot process) or the purified diastereoisomeric mixture, but disappointingly, the yields recorded for the thionolactone 12 were around 45%, significantly lower than the 85% yield reported. 47 As a byproduct, the glucono--lactone 11 was identified and actually isolated in an equal amount when the reaction time was increased thus allowing for the complete conversion of both thiosulfinate diastereoisomers 10. Formation of an undesired analogous -lactone was observed by Fairbanks (~20% yield) during the thermal elimination at 120°C of a rhamno-configured thiosulfinate.…”

A Journey into Recent Microwave‐Assisted Carbohydrate Chemistry

“…Yang and co-workers [32] developed an MW-assisted cross-coupling reaction of perbenzylated pyranoid glycals (27) with aryl bromides (53) in the presence of catalytic amounts (5 mol %) of Pd(OAc) 2 in N,N -dimethylformamide (DMF) to produce 2 ,3 -unsaturated C-aryl-α-glycopyranosides (54) in a rapid, readily applicable, and stereospecific manner. Compared with the known techniques, this fast, high-yielding, and stereospecific procedure offers a more practical approach to Heck-type C-aryl glycosylation (scheme 21.14).…”

“…Wilkinson and Fairbanks [53] accomplished the synthesis of carbohydrate thionolactones 69 and 70 from the corresponding 1-thio sugar (67) involving the in situ formation of a thiosulfinate intermediate 68, by treatment of the thiol with commercially available sulfinyl chloride followed by thermolysis (scheme 21.20).…”