217089-55-9

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 217089-45-7 3,5-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-allofuranose 
• 217089-51-5 (3R,4S,5R)-4-Benzyloxy-5-[(R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-dihydro-furan-2-one 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 4495-04-9 1,2-O-isopropylidene-α-D-allofuranose 
• 217089-53-7 Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-[(R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Synthesis of tetrahydropyrans from sugar lactones

Dehydration of both γ- and δ- hexonolactones, either by intramolecular nucleophilic displacement of triflate leaving groups at C-2, or by Mitsunobu type displacement of the OH-6, provides access to bicyclic lactones which contain tetrahydropyran rings. Reduction or nucleophilic ring opening of these bicyclic lactones furnishes polyfunctionalised tetrahydropyrans in good yield.