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Synthesis of a library of glucal-derived triazoles via copper-catalyzed azide–alkyne cyclization

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A library of glucal-derived triazoles have been synthesized using the copper-catalyzed azide-alkyne cyclization reaction starting from 3,4,6-tri-O-acetyl-d-glucal. Different trimethylsilyl substituted alkyne derivatives of glucal were first synthesized from 3,4,6-tri-O-acetyl-d-glucal, using… Click to show full abstract

A library of glucal-derived triazoles have been synthesized using the copper-catalyzed azide-alkyne cyclization reaction starting from 3,4,6-tri-O-acetyl-d-glucal. Different trimethylsilyl substituted alkyne derivatives of glucal were first synthesized from 3,4,6-tri-O-acetyl-d-glucal, using Sonogashira coupling, hydrostannation and iodination steps. These glucal-based trimethylsilyl-protected alkynes were then used in the copper-catalyzed cyclization reactions with different organic azides to synthesize the corresponding triazole derivatives of d-glucal.

Keywords: cyclization; copper; library glucal; derived triazoles; copper catalyzed; glucal derived

Journal Title: Tetrahedron Letters
Year Published: 2017

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