Back to results
US 4,308,376 AGranted
Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
AssigneeChembiomed, Ltd.
InventorsRaymond U. Lemieux, R. Murray Ratcliffe
Life of this patent
Estimating the term…
Loading patent…
Loading patent…
AssigneeChembiomed, Ltd.
InventorsRaymond U. Lemieux, R. Murray Ratcliffe
Estimating the term…
O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
A process which comprises:
A process which comprises:
A process which comprises displacing the nitrate group of an acylated 2-azido-2-deoxy glycosyl nitrate with an acyl group, reducing the azido group to amine and hydrolyzing with an aqueous mineral acid to produce the salt of the 2-amino-2-deoxy glycose.
A process which comprises displacing the nitrate group of an acylated 2-azido-2-deoxy glycosyl nitrate with an acyl group, hydrolyzing the product and reducing the azido group of the hydrolyzed product to amine.
The process which comprises reacting an anomeric mixture of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrate with sodium acetate in acetic acid to form the 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl acetates, isolating said product, hydrolyzing said isolated product in an aqueous acid to provide 2-azido-2-deoxy-D-galactose, and reducing the 2-azido-2-deoxy-D-galactose in the presence of a molar equivalent of acid to produce the corresponding acid salt of D-galactosamine.
The process which comprises reacting an anomeric mixture of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrate with sodium acetate in acetic acid to form the 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl acetates, isolating said product, hydrolyzing said isolated product in an aqueous acid to provide 2-azido-2-deoxy-D-galactose, and reducing the 2-azido-2-deoxy-D-galactose and then N-acetylating the D-galactosamine product to form N-acetyl-D-galactosamine.
The process which comprises reacting an anomeric mixture of 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-2-a zido-2-deoxy-D-glucopyranosyl nitrate with sodium acetate in acetic acid to replace the nitrate, reducing the azide, acetylating the product and de-O-acetylating to form N-acetyllactosamine.
A process for preparing 2-acetamido-2-deoxy glycoses from acylated-2-azido-2-deoxy glycosyl nitrates comprising:
Dependencies are inferred from the claim text.