Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides.
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.
Ronchi
Paolo
P
Dipartimento di Chimica Organica e Industriale and Centro Interdisciplinare Studi Bio-molecolari e Applicazioni Industriali (CISI), Università degli Studi di Milano, Milano, Italy.
Vignando
Stefano
S
Guglieri
Sara
S
Polito
Laura
L
Lay
Luigi
L
D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D007455:Iodine / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013379:Substrate Specificity
D000475:Alkenes; D009844:Oligosaccharides; D007455:Iodine