Literature DB >> 12790566

Synthesis and reactions of fluorous carbobenzyloxy (FCbz) derivatives of alpha-amino acids.

Dennis P Curran1, Muriel Amatore, David Guthrie, Matthew Campbell, Eisan Go, Zhiyong Luo.   

Abstract

Fluorous carbobenzyloxy ((F)Cbz) reagents RfCH(2)CH(2)C(6)H(4)CH(2)OC(O)OSu (where Su is succinimidoyl and Rf is C(6)F(13) and C(8)F(17)) have been used to make (F)Cbz derivatives of 18 of the 20 natural amino acids. The potential utility of this new family of reagents in both standard fluorous synthesis with spe separation and fluorous quasiracemic synthesis is illustrated with representative reactions of the (F)Cbz-Phe derivatives.

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Year:  2003        PMID: 12790566     DOI: 10.1021/jo0344283

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  8 in total

Review 1.  Fluorous synthesis of heterocyclic systems.

Authors:  Wei Zhang
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

2.  Synthetic applications of fluorous solid-phase extraction (F-SPE).

Authors:  Wei Zhang; Dennis P Curran
Journal:  Tetrahedron       Date:  2006-12-18       Impact factor: 2.457

Review 3.  Fluorous tagging strategy for solution-phase synthesis of small molecules, peptides and oligosaccharides.

Authors:  Wei Zhang
Journal:  Curr Opin Drug Discov Devel       Date:  2004-11

4.  Plate-to-plate fluorous solid-phase extraction for solution-phase parallel synthesis.

Authors:  Wei Zhang; Yimin Lu; Tadamichi Nagashima
Journal:  J Comb Chem       Date:  2005 Nov-Dec

5.  Fluorous parallel synthesis of a hydantoin/thiohydantoin library.

Authors:  Yimin Lu; Wei Zhang
Journal:  Mol Divers       Date:  2005       Impact factor: 2.943

6.  Automation of fluorous solid-phase extraction for parallel synthesis.

Authors:  Wei Zhang; Yimin Lu
Journal:  J Comb Chem       Date:  2006 Nov-Dec

7.  Fluorous synthesis of hydantoins and thiohydantoins.

Authors:  Wei Zhang; Yimin Lu
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

8.  Fluorous Mixture Synthesis (FMS) of Enantiomers, Diastereomers, and Compound Libraries.

Authors:  Wei Zhang
Journal:  ARKIVOC       Date:  2004-05-28       Impact factor: 1.140

  8 in total

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