903570-37-6Relevant articles and documents
2-(Phenylthio)ethyl as a novel two-stage base protecting group for thymidine analogues
D'Onofrio, Jennifer,De Napoli, Lorenzo,Di Fabio, Giovanni,Montesarchio, Daniela
, p. 845 - 848 (2007/10/03)
2-(Phenylthio)ethyl is here proposed for temporary masking the thymine residue in the synthesis of sugar modified thymidine derivatives. This protection has been devised as a 'two-stage' system. The 2-(phenylthio)ethyl residue can be easily and regiospecifically inserted at the N3-position of the pyrimidine by a Mitsunobu reaction with 2-(phenylthio)ethanol and is perfectly stable also to strongly basic conditions. This allowed us to selectively achieve O-alkylation of the ribose moieties in satisfactory yields, avoiding undesired base alkylations. After oxidation of the thioether to sulfone, the thymine protecting group can be totally removed, by a β-elimination mechanism, upon the same basic treatment required for the final deprotection and detachment of oligonucleotides from the support in solid-phase synthesis protocols. Georg Thieme Verlag Stuttgart.