Saccharoascorbic acid derivatives and production thereof

Details Saccharoascorbic acid derivatives and production thereof Saccharoascorbic acid derivatives and production thereof

1990-01-31

1991-08-27

Bond, Robert T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548317, 546214, 540480, 540596, 252407, 514473, C07D30762, A61K 3134

Patent

active

050434594

ABSTRACT:
This invention relates to novel saccharoascorbic acid derivatives and their production. The derivatives are represented by the general formula set forth below, for example, an amido, a thioester or carboxylic ester of saccharoascorbic acid, and their salts.
The compounds of the present invention are useful for food additives as antioxidants, an intermediate for the production of dichiral compounds and medicines having antithrombotic activity. ##STR1## wherein Z represents ##STR2## --SR.sub.6 or --OR.sub.7, R.sub.4 and R.sub.5 independently represent hydrogen or a hydrocarbon group of 1 to 24 carbon atoms, or R.sub.4 and R.sub.5 may together form --CH.sub.2 --.sub.n in which n is an integer of 4 to 7, R.sub.6 represents a hydrocarbon group of 1 to 24 carbon atoms, R.sub.7 represents hydrogen or a hydrocarbon group of 1 to 24 carbon atoms, R.sub.1, R.sub.2 and R.sub.3 independently represent hydrogen, an acyl group of 1 to 18 carbon atoms or a hydrocarbon group of 1 to 24 carbon atoms, and .about. represents the R-configration or the S-configration; provided that when Z is --OR.sub.7, R.sub.1 and R.sub.2 are not the same and R.sub.3 is hydrogen, or a salt thereof.

REFERENCES:
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patent: 2483251 (1949-09-01), Trenner
patent: 4837020 (1989-06-01), Mise et al.
Noller, "Chemistry of Organic Compounds" 2nd Ed. (1957) (Saunders) pp. 244-245, 278.
Kosai et al., Chem. Abstr., vol. 97, No. 7, Aug. 16, 1982, p. 631, Abstract No. 55611h.
Bayeyeno-Volant et al., Chem. Abstr., vol. 105, No. 4, Jul. 28, 1986, Abstract No. 33320u.
Stuber et al., Carbohydrate Research, 60 (1978), pp. 251-258.
Takamura et al., Vitamins, 56(3) pp. 117-131 (1982).

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