Literature DB >> 16448132

A comprehensive approach to the synthesis of sulfate esters.

Levi S Simpson1, Theodore S Widlanski.   

Abstract

A comprehensive approach to the synthesis of sulfate esters was developed. This approach permits the direct and high-yielding synthesis of protected sulfate monoesters. Subsequent deblocking to reveal sulfate monoesters is accomplished in near-quantitative yield. The exceptionally stable neopentyl protecting group and the labile isobutyl protecting group were utilized in the synthesis of aromatic and aliphatic sulfate monoesters. Strategies for tuning protecting group reactivity were also explored and developed.

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Year:  2006        PMID: 16448132     DOI: 10.1021/ja056086j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  25 in total

1.  Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds.

Authors:  Arjun Raghuraman; Muhammad Riaz; Michael Hindle; Umesh R Desai
Journal:  Tetrahedron Lett       Date:  2007-09-17       Impact factor: 2.415

2.  Rapid assembly and profiling of an anticoagulant sulfoprotein library.

Authors:  Emma E Watson; Jorge Ripoll-Rozada; Ashley C Lee; Mike C L Wu; Charlotte Franck; Tim Pasch; Bhavesh Premdjee; Jessica Sayers; Maria F Pinto; Pedro M Martins; Shaun P Jackson; Pedro José Barbosa Pereira; Richard J Payne
Journal:  Proc Natl Acad Sci U S A       Date:  2019-06-20       Impact factor: 11.205

3.  Chemical Sulfation of Small Molecules - Advances and Challenges.

Authors:  Rami A Al-Horani; Umesh R Desai
Journal:  Tetrahedron       Date:  2010-04-17       Impact factor: 2.457

4.  A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore.

Authors:  Steven M Pauff; Stephen C Miller
Journal:  J Org Chem       Date:  2012-12-13       Impact factor: 4.354

5.  Synthesis of Sulfotyrosine-Containing Peptides by Incorporating Fluorosulfated Tyrosine Using an Fmoc-Based Solid-Phase Strategy.

Authors:  Wentao Chen; Jiajia Dong; Suhua Li; Yu Liu; Yujia Wang; Leonard Yoon; Peng Wu; K Barry Sharpless; Jeffery W Kelly
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

6.  On designing non-saccharide, allosteric activators of antithrombin.

Authors:  Arjun Raghuraman; Aiye Liang; Chandravel Krishnasamy; Trish Lauck; Gunnar T Gunnarsson; Umesh R Desai
Journal:  Eur J Med Chem       Date:  2008-10-09       Impact factor: 6.514

7.  Solid-phase synthesis of alpha-glucosamine sulfoforms with fragmentation analysis by tandem mass spectrometry.

Authors:  Runhui Liu; Chamnongsak Chanthamontri; Hongling Han; Jesús M Hernández-Torres; Karl V Wood; Scott A McLuckey; Alexander Wei
Journal:  J Org Chem       Date:  2008-07-09       Impact factor: 4.354

8.  Chemically modified peptides based on the membrane-proximal external region of the HIV-1 envelope induce high-titer, epitope-specific nonneutralizing antibodies in rabbits.

Authors:  Vincent J Venditto; Lindsay Wieczorek; Sebastian Molnar; Fernando Teque; Gary Landucci; Douglas S Watson; Donald Forthal; Victoria R Polonis; Jay A Levy; Francis C Szoka
Journal:  Clin Vaccine Immunol       Date:  2014-05-28

9.  An efficient approach to sulfate metabolites of polychlorinated biphenyls.

Authors:  Xueshu Li; Sean Parkin; Michael W Duffel; Larry W Robertson; Hans-Joachim Lehmler
Journal:  Environ Int       Date:  2009-04-05       Impact factor: 9.621

10.  Template-constrained cyclic sulfopeptide HIV-1 entry inhibitors.

Authors:  Jonathan G Rudick; Meg M Laakso; Ashley C Schloss; William F DeGrado
Journal:  Org Biomol Chem       Date:  2013-11-07       Impact factor: 3.876

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