Glucose-derived 3'-(carboxymethyl)-3'-deoxyribonucleosides and 2', 3'-lactones as synthetic precursors for amide-linked oligonucleotide analogues.
Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.
Robins
M J
MJ
Department of Chemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Doboszewski
B
B
Timoshchuk
V A
VA
Peterson
M A
MA
D003839:Deoxyadenosines / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009841:Oligonucleotides / Q000138:chemical synthesis*; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D003839:Deoxyadenosines; D007202:Indicators and Reagents; D007783:Lactones; D009841:Oligonucleotides; D005947:Glucose; D013936:Thymidine