Solid-phase synthesis of cyclic C-glycoside/amino acid hybrids by carbamate coupling chemistry and on-support cyclization



: Katajisto J, Lonnberg H

Publisher: WILEY-V C H VERLAG GMBH

: 2005

European Journal of Organic Chemistry

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

: EUR J ORG CHEM

: 2005

: 16

: 3518

: 3525

: 8

: 1434-193X

DOI: https://doi.org/10.1002/ejoc.200500273


A solid-supported synthesis of cyclic C-glycoside/amino acid conjugates is described. For this purpose, N-(tert-butoxycarbonyl)-[6-O-(p-nitrophenoxycarbonyl)-2,3,4-tri-O-(p-toluoyl)- beta-D-glycopyranosyl]methylamines derived from galactose and glucose were prepared and used as activated monomers together with appropriately protected amino acids. The solid phase assembly of the linear precursor was conducted by alternating peptide and carbamate coupling, using glutamate immobilized through its gamma-carboxy function to a SCAL linker as a handle. On-support cyclization followed by cleavage from the support gave the desired conjugates. Removal of the p-toluoyl protections was carried out in solution phase by methoxide ion-catalyzed transesterification in methanol.



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