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Molecules 2009, 14(12), 5298-5307; doi:10.3390/molecules14125298
Article

Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars

1,2, 1,2, 1,*  and 2,*
1 Malaghan Institute of Medical Research, P.O. Box 7060, Wellington, New Zealand 2 School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand
* Authors to whom correspondence should be addressed.
Received: 13 November 2009 / Revised: 15 December 2009 / Accepted: 15 December 2009 / Published: 16 December 2009
(This article belongs to the Special Issue Asymmetric Synthesis)
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Abstract

The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino-L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation methodologies to the synthesis of 2-deoxy-aza-sugars. The carbamate annulation occurred with excellent yield and diastereoselectively (>20:1 d.r.), in favour of the 3,4-cis isomer.
Keywords: aza-sugar; glycosidase inhibitors; asymmetric; reductive amination; carbamate aza-sugar; glycosidase inhibitors; asymmetric; reductive amination; carbamate
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Dangerfield, E.M.; Plunkett, C.H.; Stocker, B.L.; Timmer, M.S.M. Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars. Molecules 2009, 14, 5298-5307.

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