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

1978-04-07

1980-03-25

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

424180, 536 4, 536 53, 536115, 536119, 536122, C07H 1102

Patent

active

041951743

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: 3935184 (1976-01-01), Jones et al.
patent: 3953422 (1976-04-01), Pfeiffer
patent: 4039663 (1977-08-01), Areamone et al.
patent: 4064339 (1977-12-01), Coussediere et al.
patent: 4105760 (1978-08-01), Szejtli et al.

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