89157-91-5

Upstream product

• 253328-56-2 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose 
• 108-24-7 acetic anhydride 
• 19684-32-3 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 28235-34-9 2,3,4-tri-O-acetyl-1,6-anhydro-β-L-idopyranose 
• 253328-56-2 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose 
• 848310-21-4 (4-nitro)phenyl 2,3,5,6-tetra-O-acetyl-α-L-idofuranoside 
• 848310-29-2 (4-nitro)phenyl 2,3,5,6-tetra-O-acetyl-β-L-idofuranoside 
• 848309-89-7 (4-nitro)phenyl α-L-idofuranoside 

Relevant academic research and scientific papers

The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides

Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.

Regioselective mono-oxidation of Non-protected carbohydrates by brominolysis of the tin intermediates

Most of the glycosides examined were smoothly oxidized by the bis-tributyltin oxide-bromine method without protection of the other hydroxyl groups to the mono-oxo derivatives in high yield and with high regioselectivity.The regioselectivity (position of oxidation) can be predicted from two independent rules: anomeric control (the oxidation takes place at C-3 for the glycosides which have an equatorial glycosidic linkage and at C-4 for those which have an axial glycosidic linkage) and axial oxidation for cis-1,2 glycols.Keywords - carbohydrate; glycoside; oxidation; regioselective oxidation; bis-tributyltin oxide-bromine; dibutyltin oxide-bromine; brominolysis; oxo-glycoside; 13C-NMR.