203717-53-7

Upstream product

• 76375-66-1 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 58341-66-5 methyl 2,6-di-O-benzyl-α-D-glucopyranoside 
• 141-78-6 ethyl acetate 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 15038-71-8 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 99212-41-6 methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 688341-33-5 methyl 4-azido-2,6-di-O-benzyl-4-deoxy-α-D-galactopyranoside 
• 688341-52-8 Acetic acid (2S,3R,4R,5R,6R)-3-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

Monoacetylation of carbohydrate diols via transesterification with ethyl acetate

Monoacetylation of secondary diols in protected monosaccharides was achieved with ethyl acetate as acyl donor and sodium tert-butoxide as a base. The regioseletivity of the reaction varied depending on the substrate. This new method provides a simple, fast, and efficient method to access selectively acetylated carbohydrates that is compatible with acid-sensitive protecting groups. CSIRO 2014.

Regioselective reductive ring opening of benzylidene acetals using triethylsilane and iodine

Novel reaction conditions have been developed for the regioselective reductive ring opening of benzylidene acetals in carbohydrate derivatives using triethylsilane and molecular iodine. The reaction is fast, compatible with most of the functional groups e

A New reaction for the direct conversion of 4-azido-4-deoxy-D-galactoside into a 4-deoxy-D-erythro-hexos-3-ulose

A new one-step reaction has been developed for converting 4-azido-4-deoxy-D-galactoside into 4-deoxy-D-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the

Synthesis, NMR spectroscopy and conformational studies of the four anomeric methyl glycosides of the trisaccharide D-Glcp-(1→3)-[D-Glcp-(1→4)]-α-D-Glcp

The four anomeric methyl glycosides of the vicinally disubstituted trisaccharide D-Glcp-(1→3)-[D-Glcp-(1→4)]-α-D-Glcp have been synthesized using silver trifluoromethanesulfonate mediated glycosylations. The 1H and 13C NMR resonances have been assigned and used for extraction of glycosylation shifts, i.e. the differences between chemical shifts for signals from the trisaccharides and those of the respective monomers, as well as those derived by addition of the glycosylation shifts for each disaccharide element. Glycosylation shifts are up to 0.5 ppm for proton and 10 ppm for carbon. Deviations from additivity are -0.2-0.1 ppm for proton and -4.5-2.3 ppm for carbon, usually confined to the atoms at the linkage positions. The conformational space spanned for the trisaccharides, and the constituent disaccharides, has been investigated by Metropolis Monte Carlo simulations using the HSEA force field. The α-linked glucosyl groups show larger conformational changes with multiple energy minima, whereas the β-linked glucosyl groups have a single energy minimum, close to that identified for the constituent disaccharide.