369386-52-7

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 863997-29-9 ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-1-thio-β-D-glucopyranoside 
• 112929-24-5 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose 
• 863997-32-4 ethyl 2-allyloxycarbonylamino-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 863997-33-5 ethyl 2-amino-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 863997-30-2 ethyl 2-allyloxycarbonylamino-2-deoxy-3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 369386-55-0 ethyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

An alternative high yielding and highly stereoselective method for preparing an α-Neu5NAc-(2,6)-D-GalN3 building block suitable for further glycosylation

This paper deals with new approaches to α-Neu5NAc-(2,6)-D-GalN 3 building blocks, suitable as glycosylation donors. The major improvement, by comparison with the results of the literature, lies in the glycosylation step of a new D-galactosamine acceptor (tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside) with O-methyl-S- [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D- galacto-non-2-ulopyranosyl)onate] dithiocarbonate as the N-acetylneuraminic acid donor. The reaction affords the expected disaccharide in high yield (85%) and a complete α-Neu5NAc stereoselectivity. A subsequent oxidation step, eliminating the glycal by-product allows an easier purification. Afterwards, the tert-butyldimethylsilyl disaccharide can be transformed into a donor, after cleavage of the anomeric group in smooth conditions.