An approach to the stereoselective synthesis of Sp-dinucleoside phosphorothioates using phosphotriester chemistry
1987; Oxford University Press; Volume: 15; Issue: 23 Linguagem: Inglês
10.1093/nar/15.23.9921
ISSN1362-4962
AutoresRichard Cosstick, David M. Williams,
Tópico(s)Advanced biosensing and bioanalysis techniques
ResumoAn approach to the stereoselective synthesis of Sp- dinucleoside phosphorothioates has been investigated which utilizes phosphotriester chemistry. The stereoselectivity of internucleotide bond formation between N -benzoyl-5′- 0 -(4,4′-dimethoxytrityl)-2′-deoxycytidine-3′- 0 -( S 2-cyanoethyl) phosphorothioate ( 3 ) and 3′-O-acetylthymidine has been studied using either mesitylenesulphonyl-5-(pyridin-2-yl)tetrazole (MSPy) or 1-mesitylenesulphonyl- 3-nitro-l,2,4-triazole (MSNT) as the activating agent. The removal of the cyanoethyl group from the protected dinucleoside phosphorothioate has been studied, and conditions are reported which provide rapid deprotection without concomittant desulphurisation.
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