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

0450014 - ÚOCHB 2016 RIV US eng J - Journal Article
Downey, Alan Michael - Richter, C. - Pohl, Radek - Mahrwald, R. - Hocek, Michal
Direct One-Pot Synthesis of Nucleosides from Unprotected or 5-O-Monoprotected D-Ribose.
Organic Letters. Roč. 17, č. 18 (2015), s. 4604-4607. ISSN 1523-7060. E-ISSN 1523-7052
R&D Projects: GA ČR GAP207/11/0344
Institutional support: RVO:61388963
Keywords : nucleosides * cytostatics * biological activity
Subject RIV: CC - Organic Chemistry
Impact factor: 6.732, year: 2015
http://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5b02332

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 nudeobases. Using modified Mitsunobu conditions, we report on the first direct glycosylation of purine and pyrimidine nudeobases with unprotected D-ribose to provide, beta-pyranosyl nucleosides and a one-pot strategy to yield beta-furanosides from the heterocycle and 5-O-monoprotected D-ribose.
Permanent Link: http://hdl.handle.net/11104/0251424