Synthesis of a Thioglucoside and Its Tetracyclic Conjugate Based on 6-Bromo-1,4-naphthoquinone Derivatives

A bromine-containing naphthoquinone–carbohydrate conjugate has been synthesized for the first time by intramolecular condensation of 6-bromo-2-methoxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl tetra- O -acetyl­thioglucoside by the action of sodium methoxide in methanol. The heterocyclization was accompan...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2023-04, Vol.59 (4), p.573-580
Main Authors: Polonik, S. G., Popov, R. S., Makhankov, V. V., Sabutski, Yu. E.
Format: Article
Language:English
Subjects:
Bromine
Carbohydrates
Chemistry
Chemistry and Materials Science
Conjugates
Organic Chemistry
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Summary:A bromine-containing naphthoquinone–carbohydrate conjugate has been synthesized for the first time by intramolecular condensation of 6-bromo-2-methoxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl tetra- O -acetyl­thioglucoside by the action of sodium methoxide in methanol. The heterocyclization was accompanied by substitution of the thioglucoside moiety by methoxy group, followed by the formation of regioisomeric conjugate.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023040036