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.

2-(Phenylthio)-ethyl as a novel two-stage base protecting group for thymine analogues / J., D'Onofrio; DE NAPOLI, Lorenzo; DI FABIO, Giovanni; Montesarchio, Daniela. - In: SYNLETT. - ISSN 0936-5214. - ELETTRONICO. - 6:6(2006), pp. 845-848. [10.1055/s-2006-933147]

2-(Phenylthio)-ethyl as a novel two-stage base protecting group for thymine analogues

DE NAPOLI, LORENZO;DI FABIO, GIOVANNI;MONTESARCHIO, DANIELA
2006

Abstract

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.
2006
2-(Phenylthio)-ethyl as a novel two-stage base protecting group for thymine analogues / J., D'Onofrio; DE NAPOLI, Lorenzo; DI FABIO, Giovanni; Montesarchio, Daniela. - In: SYNLETT. - ISSN 0936-5214. - ELETTRONICO. - 6:6(2006), pp. 845-848. [10.1055/s-2006-933147]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/103512
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 10
  • ???jsp.display-item.citation.isi??? 8
social impact