Stereoselective synthesis of S-linked α(2â8) and α(2â8)/α(2â9) hexasialic acids.
J Am Chem Soc
; 134(38): 16074-9, 2012 Sep 26.
Article
em En
| MEDLINE
| ID: mdl-22957651
ABSTRACT
A new approach for the synthesis of S-linked α(2â8) and alternating α(2â8)/α(2â9) oligosialic acids by S-alkylation has been developed, using chemo- and stereoselective alkylation of a C2-thiolated sialoside donor (nucleophile) with either a C8- or C9-iodide-activated sialoside acceptor (electrophile). An efficient intramolecular acetyl group migration from the C7 to C9-position of the sialoside under mild basic conditions was used to generate the C8-iodide, the key sialyl acceptor (electrophile). Using this strategy, the syntheses of S-linked α(2â8) and α(2â8)/α(2â9) hexasialic acids were achieved.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ácidos Siálicos
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article