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Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
Malaghan Institute of Medical Research, P.O. Box 7060, Wellington, New Zealand
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
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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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.
Dangerfield EM, Plunkett CH, Stocker BL, Timmer MSM. Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars. Molecules. 2009; 14(12):5298-5307.
Dangerfield, Emma Marie; Plunkett, Catherine Heather; Stocker, Bridget Louise; Timmer, Mattie Simon Maria. 2009. "Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars." Molecules 14, no. 12: 5298-5307.