13992-18-2

Upstream product

• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 108681-43-2 phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-α-D-mannopyranoside 

Downstream Products

• 108681-44-3 (3aS,4R,5aR,9aR,9bS)-4-Benzenesulfonyl-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine 
• 108681-45-4 2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol 

Relevant academic research and scientific papers

VINYL SULPHONES DERIVED FROM THIOGLYCOSIDES: SYNTHESIS AND ALKYLATION

Vinyl sulphones (1-sulfonyl glycals) are formed in good yield by elimination of propanone from 2,3-O-isopropylidene derivatives of D-mannopyranosyl and L-rhamnopyranosyl sulphones.Attempted conjugate addition of carbon nucleophiles to these vinyl sulphones, which are deactivated towards nucleophiles by the ring oxygen atom, was unsuccessful but lithiation followed by methylation yielded the 2-methyl vinyl sulphone derivatives when t-butyl sulphones rather than phenyl sulphones were used.