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• Dangerfield, E
• Plunkett, C
• Stocker, B
• Timmer, M
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• Dangerfield, E
• Plunkett, C
• Stocker, B
• Timmer, M
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• Dangerfield, E
• Plunkett, C
• Stocker, B
• Timmer, M

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

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.

Received: 13 November 2009; in revised form: 15 December 2009 / Accepted: 15 December 2009 / Published: 16 December 2009

(This article belongs to the Special Issue Asymmetric Synthesis)

Download PDF Full-Text [197 KB, uploaded 16 December 2009 11:56 CET]

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

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