156944-01-3

Upstream product

• 156944-00-2 (3R,4R,5R)-4-Benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-3-hydroxy-dihydro-furan-2-one 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 217089-43-5 (3R,4R,5R)-4-Benzyloxy-5-[(R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-dihydro-furan-2-one 
• 110920-92-8 (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol 

Downstream Products

• 156944-04-6 (2S,3S,4R)-3-Benzyloxy-4-[(R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxetane-2-carboxylic acid methyl ester 
• 217089-63-9 (1S,4R,5R,8S)-4,8-Bis-benzyloxy-2,6-dioxa-bicyclo[3.2.1]octan-7-one 
• 156944-02-4 Trifluoro-methanesulfonic acid (3R,4S,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-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.

Tetrahydropyran Derivatives from γ- and δ-Hexonolactones

Both δ- and γ-hexonolactones provide templates for the construction of bicyclic lactones in which a new tetrahydropyran ring has been formed from overall elimination of water from the C-2 and C-6 hydroxyl groups.Such studies may provide a strategy for the syntheis of C-glycosides from elimination of water between C-2 and C-6 of heptonolactones.