Literature DB >> 11082018

Mild and efficient functionalization at C6 of purine 2'-deoxynucleosides and ribonucleosides.

X Lin1, M J Robins.   

Abstract

[reaction: see text] Treatment of sugar-protected inosine and 2'-deoxyinosine derivatives with a cyclic secondary amine or imidazole and I(2)/Ph(3)P/EtN(i-Pr)(2)/(CH(2)Cl(2) or toluene) gave quantitative conversions into 6-N-(substituted)purine nucleosides. S(N)Ar reactions with 6-(imidazol-1-yl) derivatives gave 6-(N, O, or S)-substituted products. The 6-(benzylsulfonyl) group underwent S(N)Ar displacement with an arylamine at ambient temperature.

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Year:  2000        PMID： 11082018     DOI： 10.1021/ol000255h

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


  9 in total

1.  Synthetic utility of an isolable nucleoside phosphonium salt.

Authors:  Suyeal Bae; Mahesh K Lakshman
Journal:  Org Lett       Date:  2008-05-13       Impact factor: 6.005

2.  Two-step, one-pot synthesis of inosine, guanosine, and 2'-deoxyguanosine O6-ethers via intermediate O6-(benzotriazol-1-yl) derivatives.

Authors:  Hari Prasad Kokatla; Mahesh K Lakshman
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2012-06

3.  One-pot etherification of purine nucleosides and pyrimidines.

Authors:  Hari Prasad Kokatla; Mahesh K Lakshman
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

4.  Facile Modifications at the C4 Position of Pyrimidine Nucleosides via In Situ Amide Activation with 1H-Benzotriazol-1-yloxy-tris(dimethyl-amino)phosphonium Hexafluorophosphate.

Authors:  Hari K Akula; Mahesh K Lakshman
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2019-01-28

5.  A simple method for C-6 modification of guanine nucleosides.

Authors:  Mahesh K Lakshman; Josh Frank
Journal:  Org Biomol Chem       Date:  2009-06-01       Impact factor: 3.876

6.  Synthesis of N6 ,N6-Dialkyl Adenine Nucleosides With In Situ Formed Hexaalkylphosphorus Triamides.

Authors:  Mahesh K Lakshman; Asad Choudhury; Suyeal Bae; Eliezer Rochttis; Padmanava Pradhan; Amit Kumar
Journal:  European J Org Chem       Date:  2009-01-01

7.  Simple Synthesis of Amides and Weinreb Amides via Use of PPh3 or Polymer-Supported PPh3 and Iodine.

Authors:  Amit Kumar; Hari Kiran Akula; Mahesh K Lakshman
Journal:  European J Org Chem       Date:  2010-05

8.  Synthesis of Triazole-Linked SAM-Adenosine Conjugates: Functionalization of Adenosine at N-1 or N-6 Position without Protecting Groups.

Authors:  Colette Atdjian; Dylan Coelho; Laura Iannazzo; Mélanie Ethève-Quelquejeu; Emmanuelle Braud
Journal:  Molecules       Date:  2020-07-16       Impact factor: 4.411

9.  The "Speedy" Synthesis of Atom-Specific (15)N Imino/Amido-Labeled RNA.

Authors:  Sandro Neuner; Tobias Santner; Christoph Kreutz; Ronald Micura
Journal:  Chemistry       Date:  2015-06-17       Impact factor: 5.236
  9 in total

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