Selective etherification

Details Selective etherification Selective etherification

1990-01-19

1991-04-16

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549264, C07D30762

Patent

active

050084054

ABSTRACT:
There is disclosed an improved process for substitution of the hydroxy group at 2-position of an ascorbic acid derivative according to the following reaction scheme: ##STR1## wherein R.sup.0 is hydrogen, alkyl having 1 to 6 carbon atoms, phenyl or a group of the formula ##STR2## (wherein X is two hydrogen atoms, or acetal or ketal residue); R.sup.1 is an alkyl or alkenyl group having up to 22 carbon atoms which may be substituted with phenyl or alkoxy having 1 to 22 carbon atoms; Y is halogen or optionally substituted sulfonyloxy; R is hydrogen, or primary, secondary or tertiary alkyl having 1 to 10 carbon atoms; and Z is an alkali metal or an alkali earth metal. There is also disclosed hydrolysis of the following scheme: ##STR3## wherein R.sup.1 is as defined above; and X is acetal or ketal residue.

REFERENCES:
patent: 4552888 (1985-11-01), Koppel et al.
Kaneyoshi Kato et al., "Studies on Scavengers of Active Oxygen Species, 1. Synthesis and Biological Activity of 2-O-Alkyl-Ascorbic Acids," J. Med. Chem. 1988, 31, pp. 793-798.
P. A. Seib, et al., J. Chem. Soc., Perkin I, "Synthesis and Stability of L-Ascorbate 2-Sulphate," pp. 1220-1224 (1974).
C. H. Lee, et al., Carbohydrate Research, "Chemical Synthesis of Several Phosphoric Esters of L-Ascorbic Acid," 67, pp. 127-138, (1978).
J. Jernow, et al., Tetrahedron, "Structural Determination of Ascorbic Acid 2-O-Phosphate via Acid Hydrolysis . . . ," 35 (12), pp. 1483-1486 (1979).

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