Azidochlorination and diazidization of glycals

Details Azidochlorination and diazidization of glycals Azidochlorination and diazidization of glycals

C - Chemistry, Metallurgy

07

H

260/230.58

C07H 5/04 (2006.01) C07H 13/04 (2006.01) C07H 15/04 (2006.01) C07H 15/10 (2006.01) C07H 15/18 (2006.01)

Patent

CA 1326664

ABSTRACT OF THE DISCLOSURE A novel process is provided for the azidochlorinating a non- manno 2-deoxy hexosyl glycal element of a carbohydrate. The process includes reacting the glycal with a peroxyldisulfate salt, a ferrous salt, an azide salt and a chloride salt under conditions favouring the in situ generation of an azide-free radical, whereby an azide group is attached to the C-2 carbon of the glycal and a chloride group is attached to the C-1 carbon. Compounds, e.g., 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-D- galactopyranosyl chloride, and 3,4,6-tri-O-benzyl-2-azido-2- deoxy-alpha-beta-D-galactopyranose may be prepared from tri-O- benzyl galactal as well as 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D- alpha-galactopyranosyl chloride and 3,6,-di-O-acetyl-4-O- [2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azido-2-deoxy- alpha-D-glycopyranosyl chloride from their respective O- acetylated glycal derivatives by the addition of azido chloride which is chemically generated in situ. A process using 3,4,6- tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride for the synthesis of antigenic determinants, e.g., the terminal asialo GM1(beta-D-Gal(1->3)-beta-D-GalNAc-OR) has also been provided. The conversion of the subject synthon into 3,4,6-tri- O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide and 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose is also described. A further process for the synthetic generation of the Tn antigen (alpha-D-GalNAc-O-L-serine) is also described.

598387

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