The synthesis of the tetrasaccharide rhamnanic motif α-l-Rha-(1→3)-α-l-Rha-(1→2)-α-l-Rha-(1→ 2)-α-l-Rha and its dimerization to octasaccharide have been developed. Three different pathways toward the dimerization have been investigated; the best one was based on a [4+2]+2 stepwise condensation of a rhamnose tetrasaccharide with two rhamnosyl N-phenyl trifluoroacetimidates as glycosyl donors and on an orthogonal set of protecting groups consisting of benzoyl, levulinoyl, and allyl groups.
Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria / Bedini, Emiliano; Carabellese, Antonella; D., Comegna; DE CASTRO, Cristina; Parrilli, Michelangelo. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 62:(2006), pp. 8474-8483. [10.1016/j.tet.2006.06.084]
Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria
BEDINI, EMILIANO;CARABELLESE, ANTONELLA;DE CASTRO, CRISTINA;PARRILLI, MICHELANGELO
2006
Abstract
The synthesis of the tetrasaccharide rhamnanic motif α-l-Rha-(1→3)-α-l-Rha-(1→2)-α-l-Rha-(1→ 2)-α-l-Rha and its dimerization to octasaccharide have been developed. Three different pathways toward the dimerization have been investigated; the best one was based on a [4+2]+2 stepwise condensation of a rhamnose tetrasaccharide with two rhamnosyl N-phenyl trifluoroacetimidates as glycosyl donors and on an orthogonal set of protecting groups consisting of benzoyl, levulinoyl, and allyl groups.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
