Convergent synthesis of the methyl glycosides of a tetra- and a pentasaccharide fragment of the Shigella flexneri serotype 2a O-specific polysaccharide
| Autor: | Fabienne Segat-Dioury, Laurence A. Mulard |
|---|---|
| Přispěvatelé: | Chimie Organique, Institut Pasteur [Paris]-Centre National de la Recherche Scientifique (CNRS), Chimie Organique (UCO), Chimie des Biomolécules, Institut Pasteur [Paris] (IP)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2002 |
| Předmět: |
chemistry.chemical_classification
biology 010405 organic chemistry Stereochemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Acetal Convergent synthesis Glycoside 010402 general chemistry biology.organism_classification 01 natural sciences Catalysis 0104 chemical sciences Inorganic Chemistry Residue (chemistry) chemistry.chemical_compound Shigella flexneri chemistry Tetrasaccharide Tetra Trisaccharide Physical and Theoretical Chemistry ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Tetrahedron: Asymmetry Tetrahedron: Asymmetry, Elsevier, 2002, 13 (20), pp.2211-2222. ⟨10.1016/S0957-4166(02)00580-3⟩ Tetrahedron: Asymmetry, 2002, 13 (20), pp.2211-2222. ⟨10.1016/S0957-4166(02)00580-3⟩ |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/S0957-4166(02)00580-3⟩ |
| Popis: | International audience; The branched pentasaccharide, α-l-Rhap-(1→3)-[α-d-Glcp-(1→4)]-α-l-Rhap-(1→3)-β-d-GlcNAcp-(1→2)-α-l-Rhap (B(E)CDA) and the corresponding linear tetrasaccharide (ECDA), which are part of the Shigella flexneri serotype 2a O-antigen, were synthesized as their methyl glycosides according to a convergent strategy. The syntheses rely on the use of suitable B(E)C and EC trichloroacetimidate donors, respectively, and involve an appropriate DA acceptor which bears an isopropylidene acetal to block OH-4 and OH-6 of residue D. The preparation of the related linear CDA-OMe trisaccharide, which was used as a model, is also described.A convergent synthesis of the pentasaccharide B(E)CDA-OMe is described, together with those of the corresponding tri- and tetrasaccharide, CDA-OMe and ECDA-OMe, respectively. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect