Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars

Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars

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 metho...

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Bibliographic Details
Main Authors: Mattie Simon Maria Timmer, Bridget Louise Stocker, Emma Marie Dangerfield, Catherine Heather Plunkett
Format: Article
Language:English
Published: MDPI AG 2009-12-01
Series:Molecules
Subjects:
aza-sugar
glycosidase inhibitors
asymmetric
reductive amination
carbamate
Online Access:http://www.mdpi.com/1420-3049/14/12/5298/
Description
Summary: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.
ISSN:1420-3049

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