A versatile route for the stereoselective synthesis of oxybiotin

An efficient 10-step synthesis of oxybiotin, an oxygen analogue of biotin, is disclosed starting from 3,4,6-tri-O-benzyl-d-glucal.

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Methyl 5-((2S,3S,4R)-3,4-bis(trifluoromethylsulfonyloxy)tetrahydrofuran-2-yl)pentanoateC12H16F6O9S2De >99%[α]D = −36.6 (c 0.18, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,4R)

Methyl 5-((2S,3S,4R)-3,4-diazidotetrahydrofuran-2-yl)pentanoateC10H16N6O3De >99%[α]D = +31.3 (c 0.15, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,4R)

(+)-OxybiotinC11H16N2O4De >99%[α]D = +57.2 (c 0.10, 1 M NaOH)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,4R)