Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction

Ramakrishna I. Anegundi; Vedavati G. Puranik; Srinivas Hotha

doi:10.1039/B716996E

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Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction†‡

Ramakrishna I. Anegundi,^a Vedavati G. Puranik^b and Srinivas Hotha*^a

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^a Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India
E-mail: s.hotha@ncl.res.in
Fax: +91 20 2590 2624
Tel: +91 20 2590 2401

^b Center for Materials Characterization, National Chemical Laboratory, Pune 411 008, India

Abstract

Various 1,2,3-triazole and 1,2,3,4-tetrazole fused multi-cyclic compounds were synthesized from carbohydrate derived azido-alkyne and azido-cyanide substrates. The acid sensitive 1,2-O-isopropylidene group of the furanosyl sugar was utilized for diversification to glycosides and nucleosides under Fischer glycosidation and Vorbruggen's conditions, respectively.

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DOI: https://doi.org/10.1039/B716996E
Article type: Paper
Submitted: 02 Nov 2007
Accepted: 07 Dec 2007
First published: 18 Jan 2008

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Org. Biomol. Chem., 2008,6, 779-786

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Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction

R. I. Anegundi, V. G. Puranik and S. Hotha, Org. Biomol. Chem., 2008, 6, 779 DOI: 10.1039/B716996E

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Organic & Biomolecular Chemistry

Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction†‡

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Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction

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