Direct One-Pot Synthesis of Nucleosides from Unprotected or 5-O-Monoprotected D-Ribose.
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.
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Gilead & IOCB Research Center, Flemingovo nám. 2, Prague-6 16610, Czech Republic.
A Michael
AM
Downey
Institute of Chemistry, Humboldt-Universität zu Berlin , Brook-Taylor Strasse 2, Berlin 12489, Germany.
Celin
C
Richter
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Gilead & IOCB Research Center, Flemingovo nám. 2, Prague-6 16610, Czech Republic.
Radek
R
Pohl
Institute of Chemistry, Humboldt-Universität zu Berlin , Brook-Taylor Strasse 2, Berlin 12489, Germany.
Rainer
R
Mahrwald
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Gilead & IOCB Research Center, Flemingovo nám. 2, Prague-6 16610, Czech Republic.|Department of Organic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 8, Prague-2 12843, Czech Republic.
Michal
M
Hocek
D006031:Glycosylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011687:Purines / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D012266:Ribose / Q000031:analogs & derivatives / Q000737:chemistry*
D009705:Nucleosides; D011687:Purines; D011743:Pyrimidines; D012266:Ribose; C030986:pyrimidine; C030985:purine