Literature DB >> 15255703

A versatile and stereocontrolled route to pyranose and furanose C-glycosides.

Joanne E Harvey1, Steven A Raw, Richard J K Taylor.   

Abstract

[reaction: see text] The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

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Year:  2004        PMID: 15255703     DOI: 10.1021/ol0490678

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  1 in total

1.  On the use of 3,5-O-benzylidene and 3,5-O-(di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and their sulfoxides as glycosyl donors for the synthesis of beta-arabinofuranosides: importance of the activation method.

Authors:  David Crich; Christian Marcus Pedersen; Albert A Bowers; Donald J Wink
Journal:  J Org Chem       Date:  2007-02-08       Impact factor: 4.354

  1 in total

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