756485-20-8

Upstream product

• 592517-47-0 (+/-)-(3aR,4R,8R,8aR)-2,2-dimethylhexahydrothiepino[4,5-d][1,3]dioxole-4,8-diol 
• 592517-48-1 6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-5-thio-D-glucopyranose 
• 65-85-0 benzoic acid 

Downstream Products

• 592517-66-3 Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester 
• 592517-58-3 4-acetoxy-6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose (S)-oxide 
• 592517-54-9 4-acetoxy-6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose (R)-oxide 
• 592517-50-5 4-acetoxy-6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose 

Relevant academic research and scientific papers

Synthesis of thiosaccharides employing the Pummerer rearrangement of tetrahydrothiopyran oxides

The Pummerer rearrangement of 1-deoxy-5-thioglucopyranose derivatives carrying acetonides at the C3,4-positions proceeded regioselectively at the C1 position by treating with TFAA in the presence of pyridine. Studies employing deuterium-labelled derivatives revealed that the reaction was induced by E2 1,2-elimination of trifluoroacetic acid of the trifluoroacetoxy sulfonium intermediate. This methodology was applied to the synthesis of an isomaltotriose derivative consisting of 5-thioglucopyranoside units.

Pummerer rearrangement of 1-deoxy-5-thioglucopyranose oxides; Novel synthesis of 5-thioglucopyranose derivatives

The Pummerer rearrangement of 3,4-O-isopropylidene-1-deoxy-5-thiopyranose oxide derivatives took place at the C1 position regioselectively to give the corresponding 5-thiopyranoses. The reaction mechanism of this reaction is also discussed.