Azines and azoles: CXXVII. Glycosylation of 5,7-dihydro-4H-pyrano-[2,3-d:6,5-d′]dipyrimidine-4,6(3H)-dione and its 5-phenyl-substituted analog View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2007-04

AUTHORS

E. V. Fedorova, V. V. Kvasha, E. P. Studentsov, A. V. Moskvin, B. A. Ivin

ABSTRACT

Glycosylation of 5-phenylpyrano[2,3-d:6,5-d′]dipyrimidine-4,6-diones through the corresponding di-O-trimethylsilyl derivative with excess 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose gives a mixture of 3-mono-and 3,7-bis(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-phenylpyrano[2,3-d:6,5-d′]dipyrimidines; in the reaction with equimolar amounts of the reactants, only the monoriboside is formed. Isomeric N,N′-disubstituted pyranodipyrimidines, as well as mixtures of their mono-and disubstituted derivatives can be separated by fractional crystallization. The alkylation of pyrano[2,3-d:6,5-d′]dipyrimidine-4,6-dione and its 5-phenyl-substituted derivative with 2-oxabutane-1,4-diyl diacetate provides an efficient procedure for the synthesis of acyclic analogs of glycosides based on pyrano[2,3-d:6,5-d′]dipyrimidines. More... »

PAGES

589-595

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070363207040159

DOI

http://dx.doi.org/10.1134/s1070363207040159

DIMENSIONS

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