Efficient synthesis of benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-ω-iodoalkanoates

The efficient synthesis of four benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-ω-iodoalkanoates {benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-3-iodopropanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-4-iodobutanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-5-iodopentanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-6-iodohexanoate} from natural or protected l-amino acids is described.

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Benzyl 2-(S)-[bis-(tert-butoxycarbonyl)amino]-5-hexenoateC23H33O6N[α]D20=-18.9 (c 0.14, MeOH)Source of chirality: protected l-glutamic acidAbsolute configuration: (2S)

Benzyl 2-(S)-[bis-(tert-butoxycarbonyl)amino]-6-hydroxyhexanoateC23H35O7N[α]D20=-16.0 (c 0.13, MeOH)Source of chirality: protected l-glutamic acidAbsolute configuration: (2S)

Benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-6-iodohexanoateC18H26O4NI[α]D25=-11.6 (c 0.1, MeOH)Source of chirality: protected l-glutamic acidAbsolute configuration: (2S)