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Asymmetric synthesis of azidotetrahydropyranols via Sharpless epoxidation

Quyen Ong, Sheetal Handa, Antonio Mete, Alison M. Hill, Keith Jones

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Abstract

An approach to the synthesis of enantiomerically pure azidotetrahydropyranols 4 involving stereospecific reduction of propargylic alcohol 7 followed by Sharpless epoxidation of the resultant alllyic alcohols 8 and 12 is presented.Epoxide 10 undergoes ring opening with trimethyl orthoformate whereas epoxide 15 undergoes the expected ring opening with azide.

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An approach to the synthesis of enantiomerically pure azidotetrahydropyranols 4 involving stereospecific reduction of propargylic alcohol 7 followed by Sharpless epoxidation of the resultant alllyic alcohols 8 and 12 is presented.Epoxide 10 undergoes ring opening with trimethyl orthoformate whereas epoxide 15 undergoes the expected ring opening with azide.

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Available abstract

An approach to the synthesis of enantiomerically pure azidotetrahydropyranols 4 involving stereospecific reduction of propargylic alcohol 7 followed by Sharpless epoxidation of the resultant alllyic alcohols 8 and 12 is presented.Epoxide 10 undergoes ring opening with trimethyl orthoformate whereas epoxide 15 undergoes the expected ring opening with azide.

Key concepts: Sharpless epoxidation, Chemistry, Epoxide, Stereospecificity, Triethyl orthoformate, Azide, Ring (chemistry), Stereochemistry

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