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Microwave‐Assisted Synthesis of C ‐4′‐(1,5‐disubstituted)‐triazole ‐ spiro‐ α ‐L‐arabinofuranosyl Nucleosides
Author(s) -
Rungta Pallavi,
Mangla Priyanka,
Maikhuri Vipin K.,
Singh Sunil K.,
Prasad Ashok K.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701111
Subject(s) - cycloaddition , chemistry , propynyl , azide , combinatorial chemistry , nucleobase , intramolecular force , stereochemistry , alkyne , nucleoside , click chemistry , triazole , 1,3 dipolar cycloaddition , 1,2,3 triazole , molecule , organic chemistry , catalysis , dna , biochemistry
The synthesis of C ‐4′‐(1,5‐disubstituted)‐triazole‐spiro‐ α ‐L‐arabinofuranosyl nucleosides has been achieved in a regio‐ and stereospecific manner by using intramolecular Huisgen 1,3‐dipolar cycloaddition reaction. The synthesis of these nucleosides necessitates the possession of azide and alkyne moieties in the same molecule, which is being employed as the precursor. Thus, the crucial step in the synthesis of targeted compound is the preparation of 1,2,3‐tri‐ O ‐acetyl‐5‐azido‐5‐deoxy‐4‐ C ‐propynyl‐ α , β ‐L‐arabinofuranose and its conversion to corresponding nucleosides via nucleobase coupling. The microwave heating of such tailor made nucleoside precursors furnishes the targeted spironucleosides, which combines conformational‐restriction concept with a triazole structural feature highly sought in drug design.