Synthesis of (5’S)-5′-C-alkyl-2′-deoxynucleosides was written by Trafelet, Huldreich;Stulz, Eugen;Leumann, Christian. And the article was included in Helvetica Chimica Acta in 2001.Recommanded Product: Isopentyltriphenylphosphonium bromide This article mentions the following:
We describe the synthesis of (5’S)-5′-C-butylthymidine, of the (5’S)-5′-C-butyl- and the (5’S)-5′-C-isopentyl derivatives of 2′-deoxy-5-methylcytidine, as well as of the corresponding cyanoethyl phosphoramidites resp. Starting from thymidin-5′-al, the alkyl chain at C(5′) is introduced via Wittig chem. to selectively yield the (Z)-olefin derivatives The secondary OH function at C(5′) is then introduced by epoxidation followed by regioselective reduction of the epoxy derivatives 4a and 4b with diisobutylaluminium hydride. In the latter step, a kinetic resolution of the diastereoisomer mixture occurs, yielding the alkylated nucleoside, with (5’S)-configuration in high diastereoisomer purity (de = 94%). The corresponding 2′-deoxy-5-methylcytidine derivatives are obtained from the protected 5′-alkylated thymidine derivatives via known base interconversion processes in excellent yields. Application of the same strategy to the purine nucleoside 2′-deoxyadenine to obtain 5′-C-butyl-2′-deoxyadenosine 25 proved to be difficult due to the sensitivity of the purine base to hydride-based reducing agents. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Recommanded Product: Isopentyltriphenylphosphonium bromide).
Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Recommanded Product: Isopentyltriphenylphosphonium bromide
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary