An approach to the synthesis of pseudo-oligosaccharides based on the cross-metathesis reaction between distinct sugar-olefins, followed by intramolecular cyclization of the obtained heterodimer, is presented. In particular, the relative efficiency of two alternative approaches, the straightforward cross-metathesis reaction and the two-step procedure (self-metathesis followed by cross- metathesis), was explored and compared for diverse sugar-olefin substrates. Some representative examples of intramolecular cyclization using iodine as an electrophilic promoter, are also reported

Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides / P. Ronchi, S. Vignando, S. Guglieri, L. Polito, L. Lay. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 2009:7(2009 May 05), pp. 2635-2644.

Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides

P. Ronchi
Primo
;
S. Vignando
Secondo
;
L. Polito
Penultimo
;
L. Lay
Ultimo
2009-05-05

Abstract

An approach to the synthesis of pseudo-oligosaccharides based on the cross-metathesis reaction between distinct sugar-olefins, followed by intramolecular cyclization of the obtained heterodimer, is presented. In particular, the relative efficiency of two alternative approaches, the straightforward cross-metathesis reaction and the two-step procedure (self-metathesis followed by cross- metathesis), was explored and compared for diverse sugar-olefin substrates. Some representative examples of intramolecular cyclization using iodine as an electrophilic promoter, are also reported
oligosaccharides ; cross-metathesis ; organic synthesis
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/145114
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