Synthesis of azide-armed α-1-C-alkyl-imino-d-xylitol derivatives as key building blocks for the preparation of iminosugar click conjugates
Azide-armed α-1-C-alkyl-imino-d-xylitol derivatives have been efficiently prepared by way of olefin cross-metathesis in eight to nine steps and in an overall yield of 19% to 26% from 2,3,4-tri-O-benzyl-d-xylopyranose. Optimization of cleavage conditions of N-NAP-protected tertiary amines using DDQ in CH2Cl2-H2O (18:1) is also reported. The iminosugars synthesized will be used as key building blocks in the synthesis of multivalent iminosugars of biological interest by way of Cu(I)-catalyzed azide-alkyne cycloaddition reaction.
Decroocq, Camille,Laparra, Laura Mamani,Rodriguez-Lucena, David,Compain, Philippe
p. 559 - 574
(2012/06/01)
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