63599-69-9Relevant academic research and scientific papers
A carbohydrate-based julia-kocienski reagent for syntheses of chain-extended and C-linked saccharides
Bull, James A.,Kunz, Horst
, p. 1185 - 1190 (2014)
The carbohydrate-derived Julia-Kocienski reagent 2-{[(3aS,4S,6R,6aR)-6- methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylsulfonyl}-1, 3-benzothiazole (6) was prepared from d-ribose and investigated in the eponymous olefination. The base-promoted generation of the Julia anion induced a rearrangement to the corresponding l-lyxose epimer 2-{[(3aS,4R,6R,6aR)-6- methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylsulfonyl}-1, 3-benzothiazole (12), which reacted readily with aldehydes and with a gluconolactone. The latter reaction furnished an exo-glycal-linked C-diglycoside. Georg Thieme Verlag Stuttgart, New York.
