The synthesis of the trisaccharide Lewis a was performed using an anomeric fluorous silyl protective group. This methodology allowed us to fully characterize each product (NMR, MS) and monitor each synthetic step (TLC). Although the product purifications could be performed by fluorous-solid-phase extraction (F-SPE) technology, standard chromatography could be used to effect purification if necessary. Trichloroethoxy carbonyl (Troc) protection of the amino group of the glucosamine moiety was found essential to allow protecting group manipulation of the fluorous protected sugar.
Synthesis of the Lewis a trisaccharide based on an anomeric silyl fluorous tag / Manzoni, Leonardo; Castelli, Riccardo. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 6:23(2004), pp. 4195-4198. [10.1021/ol048474g]
Synthesis of the Lewis a trisaccharide based on an anomeric silyl fluorous tag
Riccardo Castelli
2004-01-01
Abstract
The synthesis of the trisaccharide Lewis a was performed using an anomeric fluorous silyl protective group. This methodology allowed us to fully characterize each product (NMR, MS) and monitor each synthetic step (TLC). Although the product purifications could be performed by fluorous-solid-phase extraction (F-SPE) technology, standard chromatography could be used to effect purification if necessary. Trichloroethoxy carbonyl (Troc) protection of the amino group of the glucosamine moiety was found essential to allow protecting group manipulation of the fluorous protected sugar.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
