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protecting-group-free synthesis of 2-deoxy-aza-sugarsprotecting-group-free合成2-deoxy-aza-sugars
Molecules 2009, 14, 5298-5307; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
Emma Marie Dangerfield 1,2, Catherine Heather Plunkett 1,2, Bridget Louise Stocker 1,* and
Mattie Simon Maria Timmer 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; E-Mail: bstocker@.nz
(B.L.S.); mattie.timmer@vuw.ac.nz (M.S.M.T.).
Received: 13 November 2009; in revised form: 15 December 2009 / Accepted: 15 December 2009 /
Published: 16 December 2009
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
Introduction
Aza-sugars (also known as imino-sugars) are mimetics of native sugars whereby the ring oxygen is
replaced by a nitrogen atom. Due to their structural similarity to native carbohydrates, aza-sugars are
ab
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