“…54 Direct synthesis of the more stable glycosyl thiosulfinate from thiosugars, rather than oxi-dation of the glycosyl disulfide, partially overcomes this problem. 93…”
Section: Organic and Biomolecular Chemistry Reviewmentioning
This review explores methodologies for the preparation of glycosyl disulfides, their utility as intermediates in carbohydrate synthesis, and evaluates their biological impact in glycoscience and beyond.
“…54 Direct synthesis of the more stable glycosyl thiosulfinate from thiosugars, rather than oxi-dation of the glycosyl disulfide, partially overcomes this problem. 93…”
Section: Organic and Biomolecular Chemistry Reviewmentioning
This review explores methodologies for the preparation of glycosyl disulfides, their utility as intermediates in carbohydrate synthesis, and evaluates their biological impact in glycoscience and beyond.
“…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.…”
Spiro-glyco-heterocycles were prepared on a gram scale from a thiolactone obtained by thermolysis of a thiosulfinate. Lowering of glycaemia in diabetic rat models is pointing toward potential new treatment of type 2 diabetes.
“…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).…”
Section: Synthesis Of 2 -Deoxy C-aryl-α-and -β-Glycopyranosidesmentioning
confidence: 99%
“…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).…”
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