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  • Title: Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-L- and -D-arabinopyranosides possessing antithrombotic activity.
    Author: Bozó E, Boros S, Kuszmann J.
    Journal: Carbohydr Res; 1998 Oct; 311(4):191-202. PubMed ID: 9825522.
    Abstract:
    5-S-Benzoyl-2,3-O-isopropylidene-5-thio-L-arabinose, prepared from L-arabinose diethyl dithioacetal gave, on treatment with sodium methoxide in methanol, 4-O-benzoyl-2,3-O-isopropylidene-5-thio-L-arabinopyranose 12 which was converted into its 1-O-acetate 14. Hydrolysis of 12 in acetic acid-water afforded, after acetylation, 1,2,3-tri-O-acetyl-4-O-benzoyl-5-thio-L-arabinopyranose 17 which was transformed into 2,3-di-O-acetyl-4-O-benzoyl-5-thio-L-arabinopyranosyl bromide 20. Zemplén deacylation of 17 gave 5-thio-L-arabinopyranose which was converted via 1,2,3,4-tetra-O-acetyl-5-thio-beta-L-arabinopyranose 5 into 2,3,4-tri-O-acetyl-5-thio-beta-L-arabinopyranosyl bromide 6 and into O-(2,3,4-tri-O-acetyl-5-thio-L-arabinopyranosyl) trichloro-acetimidate 7. Glycosidation of 4-nitrophenol with 12 under the Mitsunobu conditions afforded 4-nitrophenyl 4-O-benzoyl-2,3-O-isopropylidene-5-thio-alpha- and beta-L-arabinopyranoside in a approximately 1:2 ratio. Condensation of the glycosyl donors 6, 7, 17, and 20 with 4-cyano- and 4-nitrobenzenethiol yielded, after deacylation, 4-cyano- and 4-nitrophenyl 1,5-dithio-alpha- and beta-L-arabinopyranosides 28 alpha, 28 beta, 29 alpha and 29 beta in different ratios and yields, depending on the reaction conditions applied. In a similar manner the corresponding D-isomers 30 alpha, 30 beta, 31 alpha and 31 beta were also prepared. All of these glycosides, except 28 alpha, showed a stronger oral antithrombotic effect in rats as compared to beciparcil, used as reference.
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