53438-23-6

Upstream product

• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 2873-29-2 D-glucal triacetate 
• 129094-31-1 Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-benzenesulfonyl-2-bromo-tetrahydro-pyran-3-yl ester 
• 129094-30-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-benzenesulfonyl-2-bromo-tetrahydro-pyran-3-yl ester 
• 29084-13-7 (1S)-1-benzenesulfonyl-1,5-anhydro-D-glucitol 

Relevant academic research and scientific papers

A facile and selective oxidation of sulfides to sulfones

Sulfides undergo a facile and selective oxidation to sulfones under mild conditions using a catalytic amount of osmium tetroxide and tertiary amine N-oxides (N-methylmorpholine N-oxide or trimethylamine N-oxide). Both N-oxides are equally effective. The o

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.

Application of HOF·CH3CN to the synthesis of glycosyl sulfones

A fast, complete and clean conversion of thioglycosides into glycosyl sulfones under mild acidic conditions is described, using the HOF·CH3CN complex at room temperature. This methodology affords glycosyl sulfones in high yields and in excellent purity.

Fast oxidation of thioglycosides to glycosyl sulfones using KMnO 4/CuSO4·5H2O under neutral reaction conditions

A rapid oxidation of thioglycosides to glycosyl sulfones has been achieved using a combination of KMnO4 and CuSO4·5H 2O in acetonitrile and water. This reaction protocol has many advantages compared to other methods availa

Investigations into the chemistry of some 1,6-epithio 1,6-episeleno β-D-glucopyranoses

Derivatives of 1,6-dideoxy-1,6-epithio-β-D-glucopyranose have been shown to undergo oxidation reactions to afford the corresponding sulfoxides and sulfones. The sulfoxides participate in Pummerer reactions to afford the corresponding α-acetoxy sulfides wh

Comparative photohalogenation of phenylglucopyranoside and its oxidation derivatives

The photobrominations of the peracetylated phenyl thio-1-β-D-glucopyranoside and of the corresponding sulphoxides and sulphone have been investigated. The differences observed in both substrate reactivity and substitution regioselectivity indicate an easier homolysis of the anomeric C-H bond in the thioglycoside.