108681-43-2

Upstream product

• 83-87-4 D-Mannose pentaacetate 
• 530-26-7 D-Mannose 
• 108-24-7 acetic anhydride 
• 286410-13-7 phenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-1-thio-hex-2-enopyranoside 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 108-98-5 thiophenol 
• 2873-29-2 D-glucal triacetate 
• 125472-23-3 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-sulfonyl-α-D-erythro-hex-2-enopyranoside 
• 121524-01-4 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 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 

Downstream Products

• 13992-18-2 (2R,3S,4S,5S,6R)-2-Benzenesulfonyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 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

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.

Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones

An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.

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.