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

DOI: 10.1016/S0040-4039(99)01563-4

Source and publish data:

Tetrahedron Letters p. 7911 - 7915 (1999)

Update date:2022-08-03

Topics:

Authors:

Coleman, Michael P.

Boyd, Mary K.

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Article abstract of DOI:10.1016/S0040-4039(99)01563-4

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.

Full text of DOI:10.1016/S0040-4039(99)01563-4

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