The Synthesis of some 1-glycosyl-6-nitroindoles

Add time:09/02/2019    Source:sciencedirect.com

Condensation of 6-nitroindoline with 5-O-trityl-L-arabinose, -D-fucose, -D-arabinose, or -L-rhamnose gave the corresponding 1-glycosyl-6-nitroindolines, from which, after acetylation, dehydrogenation, and removal of protecting groups, 1-α-and -β-L-arabinofuranosyl, 1-β-D-fucopyranosyl, 1-α-D-arabinopyranosyl, and 1-α-and -β-L-rhamnopyranosyl derivatives of 6-nitroindole were obtained. The configuration of the arabinose and fucose derivatives was established by p.m.r. spectroscopy. Comparison of the p.m.r. and c.d. spectra of the products obtained from the glycosyl-nitroindoles by application in sequence of periodate oxidation, borohydride reduction, and acetylation allowed assignment of the configuration of the rhamnose derivatives.

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