111476-61-0

Upstream product

• 103931-37-9 phenyl α-L-arabinopyranoside 3,4-thioncarbonate 
• 103931-42-6 Acetic acid (3aS,6S,7R,7aS)-6-phenoxy-2-thioxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 1141-01-1 phenyl β-L-arabinopyranoside 
• 103931-43-7 phenyl 3,4-dideoxy-β-D-glycero-pent-3-enopyranoside 2-acetate 
• 103931-42-6 Acetic acid (3aS,6R,7R,7aS)-6-phenoxy-2-thioxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 103931-43-7 Acetic acid (2R,3R)-2-phenoxy-3,6-dihydro-2H-pyran-3-yl ester 

Downstream Products

• 104011-39-4 phenyl 3,4-dideoxy-β-D-glycero-pentopyranoside 
• 23568-40-3 (2R,3R)-2-Phenoxy-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

Thio-sugars III. Radical catalyzed thione-thiol rearrangement of cyclic thionocarbonates on a pyranose ring: Formation of cis-arranged cyclic thiolcarbonates

Pyranoside 3,4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3,4-thiolcarbonates of cis-stereochemistry, in acceptable yields. 2,3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). Although regio-control of the product was not satisfactory in most cases, some of the results suggested that the regioselectivity of the reaction is markedly influenced by the stereochemistry of the anomeric position of the substrates. The products were converted to thioglycosides (peracetate forms) by conventional means.

SELECTIVE DEOXYGENATION VIA REGIOSELECTIVE THIOACYLATION OF NON-PROTECTED GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD

Regioselective thioacylation of some non-protected glycopyranosides ( Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, Me β-D-Xyl ) was examined by the dibutyltin oxide method, using phenoxythiocarbonyl chloride as the thioacylating agent.This method gave the mono-thionocarbonates regioselectively in high yields.Acetylation of these thionocarbonates followed by deoxygenation with tributyltin hydride smoothly gave the corresponding deoxy derivatives, except for the primary thionocarbonates.Similar treatment of the pyranosides that have a cis-vicinal glycol ( Me α-D-Gal, Me β-D-Gal, Me β-L-Ara, and Ph α-L-Ara ) led to the formation of cyclic thionocarbonates, which on acetylation followed by olefination with trimethyl phosphite afforded the unsaturated derivatives in satisfactory yields.On deacetylation and subsequent hydrogenation over platinic oxide, they gave the corresponding dideoxy derivatives quantitatively.The compounds thus prepared were identified by analyses of their proton and carbon-13 nuclear magnetic resonance spectra.Keywords - glycopyranoside; regioselective thioacylation; dibutyltin oxide; deoxygenation; cis-vicinal glycol; thionocarbonate; cyclic thionocarbonate; deoxy, dideoxy sugar; unsaturated sugar; 13C-NMR

SYNTHESIS OF SOME DEOXY, UNSATURATED, AND DIDEOXY SUGARS VIA REGIOSELECTIVE THIOACYLATION OF GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD

Treatment of non-protected glycopyranosides (Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, and Me β-D-Xyl) with dibutyltin oxide followed by thioacylation with phenoxythiocarbonyl chloride gave the mono-thionocarbonates regioselectively in high yields.Acetylation o