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

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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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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