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The S-pixyl group: an efficient photocleavable protecting group for the 5′ hydroxy function of deoxyribonucleosides

✍ Scribed by Michael P. Coleman; Mary K. Boyd

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 285 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01563-4

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✦ Synopsis

The 9-phenylthioxanthyl (S-pixyl or S-Px) group has been investigated as a photocleavable protecting group for primary alcohols, and specifically as a 5' hydroxy protecting group for deoxyribonucleosides. Several alcohols, including the four nucleosides with protected exocyclic amino functions, were protected in very good to excellent yield by treatment of 9-chloro-9-phenylthioxanthene 3 in dry pyridine to reveal the derivatized compounds. Irradiation of the protected substrates in neutral, aqueous solution regenerated the starting alcohols in excellent yield.

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