Stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates)
- 1 January 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 16 (24) , 11675-11689
- https://doi.org/10.1093/nar/16.24.11675
Abstract
An approach to the stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates) is described. Fully protected (Rp)- and (Sp)-diastereomers of MMTrTPMeTAc (3) were prepared in the stereospecific reaction of P-chiral nucleotide component 5''-O-monomethoxytritylthymidine 3''-O-[O-(4-nitrophenyl)methanephosphonate] (1) and 3''-O-acetylthymidine (2) bearing activated 5''-hydroxyl function. Deprotection of the 5''-OH group in 3 and subsequent stepwise reactions of activated 5''-OH oligonucleotide components with (Rp)- or (Sp)-isomers of 1 gav the trinucleotide MMTrTPMeTAc (4) and, subsequently, the tetranucleotide MMTrTPMeTAc (5) possessing all (Rp)- or all (Sp)-configurations at their internucleotide methanephosphonate P-atoms.This publication has 12 references indexed in Scilit:
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