Direct One-Pot Synthesis of Nucleosides from Unprotected or 5-O-Monoprotected d-Ribose | Zendy

A. Michael Downey | Zendy; Celin Richter | Zendy; Radek Pohl | Zendy; Rainer Mahrwald | Zendy; Michal Hocek | Zendy

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

Author(s) -

A. Michael Downey,

Celin Richter,

Radek Pohl,

Rainer Mahrwald,

Michal Hocek

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b02332

Subject(s) - chemistry , nucleobase , glycosylation , pyrimidine , purine , ribose , combinatorial chemistry , yield (engineering) , stereochemistry , biochemistry , enzyme , dna , materials science , metallurgy

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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