Literature DB >> 26355351

Direct One-Pot Synthesis of Nucleosides from Unprotected or 5-O-Monoprotected D-Ribose.

A Michael Downey1, Celin Richter2, Radek Pohl1, Rainer Mahrwald2, Michal Hocek1,3.   

Abstract

New, improved methods to access nucleosides are of general interest not only to organic chemists but to the greater scientific community as a whole due their key implications in life and disease. Current synthetic methods involve multistep procedures employing protected sugars in the glycosylation of nucleobases. Using modified Mitsunobu conditions, we report on the first direct glycosylation of purine and pyrimidine nucleobases with unprotected D-ribose to provide β-pyranosyl nucleosides and a one-pot strategy to yield β-furanosides from the heterocycle and 5-O-monoprotected D-ribose.

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Year:  2015        PMID: 26355351     DOI: 10.1021/acs.orglett.5b02332

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


  4 in total

1.  Meteorite-catalyzed intermolecular trans-glycosylation produces nucleosides under proton beam irradiation.

Authors:  Bruno Mattia Bizzarri; Angelica Fanelli; Michail Kapralov; Eugene Krasavin; Raffaele Saladino
Journal:  RSC Adv       Date:  2021-05-27       Impact factor: 4.036

Review 2.  Strategies toward protecting group-free glycosylation through selective activation of the anomeric center.

Authors:  A Michael Downey; Michal Hocek
Journal:  Beilstein J Org Chem       Date:  2017-06-27       Impact factor: 2.883

3.  General Principles for Yield Optimization of Nucleoside Phosphorylase-Catalyzed Transglycosylations.

Authors:  Felix Kaspar; Robert T Giessmann; Katja F Hellendahl; Peter Neubauer; Anke Wagner; Matthias Gimpel
Journal:  Chembiochem       Date:  2020-01-28       Impact factor: 3.164

Review 4.  Anomeric modification of carbohydrates using the Mitsunobu reaction.

Authors:  Julia Hain; Patrick Rollin; Werner Klaffke; Thisbe K Lindhorst
Journal:  Beilstein J Org Chem       Date:  2018-06-29       Impact factor: 2.883

  4 in total

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