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

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MDPI and ACS Style

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.

AMA Style

Dangerfield EM, Plunkett CH, Stocker BL, Timmer MSM. Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars. Molecules. 2009; 14(12):5298-5307.

Chicago/Turabian Style

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.


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