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US 4,362,720 AGranted
Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
AssigneeChembiomed, Ltd.
InventorsRaymond U. Lemieux, R. Murray Ratcliffe
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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:
The product having the structure ##STR7## where n=3-19 and R' is a lower alkoxy, monocyclic aryloxy, OH, NHNH.sub.2, or N.sub.3 group.
8-Methoxycarbonyloctyl 3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl)-2-O-(.alpha.-L-fucopy ranosyl)-.beta.-D-galactopyranoside.
The process which comprises attaching 8-methoxycarbonyloctyl-3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl )-2-O-(.alpha.-L-fucopyranosyl)-.beta.-D-galactopyranoside through an amide linkage of the carbonyl group of the 8-methoxycarbonyloctyl bridging arm to an insoluble aminated solid immunoabsorbent-type support to form an immunoabsorbent.
The immunoabsorbent comprising 8-methoxycarbonyloctyl-3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl )-2-O-(.alpha.-L-fucopyranosyl)-.beta.-D-galactopyranoside attached, through an amide linkage of the carbonyl group of the 8-methoxycarbonyloctyl bridging arm, to an insoluble aminated solid immunoabsorbent-type support.
The product having the structure ##STR8## wherein n=3-19 and R' is a lower alkoxy, monocyclic aryloxy, OH, NHNH.sub.2, or N.sub.3 group.
8-Methoxycarbonyloctyl 3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl)-.beta.-D-galactopyran oside.
The immunoabsorbent comprising 8-methoxycarbonyloctyl-3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl )-.beta.-D-galactopyranoside attached, through an amide linkage of the carbonyl group of the 8-methoxycarbonyloctyl bridging arm, to an insoluble aminated solid immunoabsorbent-type support.
Dependencies are inferred from the claim text.