Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1979-09-19
1981-12-29
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 53, 536 4, 536115, 424 11, 424 85, C07H 1102
Patent
active
043083765
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.
REFERENCES:
patent: 2094693 (1937-10-01), Wyler
patent: 3496196 (1970-02-01), Suami et al.
Paulsen et al., "Chem. Abst.", vol. 112, 1979, pp. 3190-3202.
Paulsen et al, "Carbohydrate Research", vol. 64, pp. 339-364, 1978.
Lemieux Raymond U.
Ratcliffe R. Murray
Brown Johnnie R.
Chembiomed Ltd.
Johnson Ernest P.
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