79297-68-0

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 65530-28-1 methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside 
• 79233-83-3 Imidazole-1-carbothioic acid O-[(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-(toluene-4-sulfonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl] ester 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 26922-85-0 Methyl 3-deoxy-α-D-ribo-hexopyranoside 
• 72904-78-0 methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 

Downstream Products

• 117468-12-9 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 

Relevant academic research and scientific papers

Synthesis of Deoxy Sugars. Deoxygenation by Treatment with N,N'-Thiocarbonyldiimidazole/Tri-n-butylstannane

Protected sugars containing a free hydroxyl group have been deoxygenated by conversion to the O-(imidazolylthiocarbonyl) derivative with N,N'-thiocarbonyldiimidazole followed by treatment with tri-n-butylstannane.This reaction sequence offers a mild, high-yield procedure for the deoxygenation of hexose derivatives with a hindered secondary hydroxyl group at C-3 or C-4.The primary 6-O-(imidazolylthiocarbonyl) compound obtained from 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose reacts with tri-n-butylstannane to give a mixture of the 6-deoxy sugar (31percent) and starting alcohol (57percent).