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Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides.

ABSTRACT: The TMSOTf-mediated synthesis of ?-configured spirocyclic 2-substituted-2-oxazoline ribosides was achieved using a "Ritter-like" reaction in toluene through nucleophilic addition of electron-rich nitriles to the oxacarbenium ion intermediate of 1,2;3,4-di-O-isopropylidene-?-D-psicofuranose derivatives with concomitant intramolecular trapping of the C2 hydroxymethyl group on the electrophilic nitrilium carbon. These carbohydrate-derived spirooxazolines are stable and were obtained in good yield with high stereoselectivity due to the conformational rigidity imparted by the 3,4-isopropylidene group.

SUBMITTER: Vangala M

PROVIDER: S-EPMC4685833 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides.

Vangala Madhuri M Shinde Ganesh P GP

Beilstein journal of organic chemistry 20151124

The TMSOTf-mediated synthesis of β-configured spirocyclic 2-substituted-2-oxazoline ribosides was achieved using a "Ritter-like" reaction in toluene through nucleophilic addition of electron-rich nitriles to the oxacarbenium ion intermediate of 1,2;3,4-di-O-isopropylidene-β-D-psicofuranose derivatives with concomitant intramolecular trapping of the C2 hydroxymethyl group on the electrophilic nitrilium carbon. These carbohydrate-derived spirooxazolines are stable and were obtained in good yield w ...[more]

PMID: 26734077

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