Selective desulfonylation in D-xylofuranose 3,5-disulfonates | Zendy

Pavle Hadžić | Zendy; Nada Vukojević | Zendy

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Selective desulfonylation in D-xylofuranose 3,5-disulfonates

Author(s) -

Pavle Hadžić,

Nada Vukojević

Publication year - 2001

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc0105289h

Subject(s) - sulfonyl , regioselectivity , chemistry , hydrolysis , alcohol , organic chemistry , catalysis , alkyl

A method for the preparation of D-xylofuranose derivatives with a free terminal (C5) alcohol function was developed, starting from monocyclohexylidene-3,5-disulfonyl- or 5-O-sulfonyl-3-O-methyl ester. The regioselective displacement of the C5 sulfonyl ester functionwith acetate ion in dimethylsulfoxide afforded the corresponding 5-O-acetyl-1,2-O-cyclohexylidene-3-O-sulfonyl or 5-O-acetyl-3-O-methyl- -D-xylofuranose. These esters could be readily hydrolysed into the desired 1,2,3-trisubstituted xylofuranose.

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