Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosid

Details Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosid Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosid

1979-09-19

1982-12-07

Brown, Johnnie R.

Drug, bio-affecting and body treating compositions

Conjugate or complex of monoclonal or polyclonal antibody,...

Conjugated via claimed linking group, bond, chelating agent,...

424 11, 424 85, 536 41, 536 172, 536 173, 536 177, 536 187, 536 53, 536116, 536122, 536123, A61K 3514, C07H 1306

Patent

active

043627200

ABSTRACT:
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.

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patent: 3496196 (1970-02-01), Suami et al.
patent: 3953422 (1976-04-01), Pfeiffer
patent: 4067969 (1978-01-01), Penco et al.
patent: 4137401 (1979-01-01), Lemieux et al.
patent: 4195177 (1980-03-01), Inoue et al.
patent: 4238473 (1980-12-01), Lemieux et al.
Paulsen et al., "Chem. Ber.", vol. 112, 1979, pp. 3190-3202.
Paulsen et al., "Carbohydrate Research", vol. 64, pp. 339-364, 1978.

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