Preparation of 3'-C-branched uridine analogues, suitable for conversion into functionalised 3'-C-methylene derivatives.
A novel method for preparation of 1-[2-O-(tert-butyldimethylsilyl)-3- deoxy-3-C-hydroxymethyl-5-O-monomethoxytrityl-beta-D-ribo- pentofuranosyl]uracil by hydroboration of corresponding 3'-deoxy-3'-C-methyleneuridine derivative has been developed. Further conversion of the hydroxyl function into different leaving groups was carried out to afford derivatives suitable for conversion into various 3'-C-branched uridine analogues through substitution.
Winqvist
A
A
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.
Strömberg
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R
D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis; D014498:Uracil / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C442888:1-(2-O-(tert-butyldimethylsilyl)-3- deoxy-3-C-hydroxymethyl-5-O-monomethoxytrityl-ribo- pentofuranosyl)uracil; D016376:Oligonucleotides, Antisense; D014498:Uracil; D014529:Uridine