Photolysis of Methylsulfonyl and Benzyl Protected Carbohydrates

The methanesulfonates 1-6, which are protected by cyclic or acyclic acetals, were irradiated in methanol, containing potassium iodide, with 254 nm UV light. In each case photolysis caused the replacement of the methylsulfonyl group with hydrogen. When an acetyl, benzoyl, p-tolylsulfonyl, or benzyl g...

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Veröffentlicht in:	Journal of carbohydrate chemistry 1993-09, Vol.12 (6), p.779-792
Hauptverfasser:	Liu, Xiago-Gao, Binkley, Roger W.
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Organic chemistry Preparations and properties
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	The methanesulfonates 1-6, which are protected by cyclic or acyclic acetals, were irradiated in methanol, containing potassium iodide, with 254 nm UV light. In each case photolysis caused the replacement of the methylsulfonyl group with hydrogen. When an acetyl, benzoyl, p-tolylsulfonyl, or benzyl group was present (compounds 13, 14, 15, and 16, respectively), irradiation caused removal of these groups in preference to the methyl sulfonyl group. Additional study of the benzyl protected compounds 17-19 showed that irradiation in the presence of iodide ion is an effective method for deben-zylation.
ISSN:	0732-8303 1532-2327
DOI:	10.1080/07328309308019007