Use of the methylsulfenyl cation as an activator for glycosylation reactions with alkyl (aryl) l-thioglycopyranosides: synthesis of methyl O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→ 2)-α-d-glucopyranoside, a derivative of the core trisaccharide of E. coli K12☆☆☆

Add time:09/09/2019    Source:sciencedirect.com

Methylsulfenyl bromide (MSB) and methylsulfenyl trifluoromethanesulfonate (MST) have been used to prepare 1,2-cis-linked disaccharides. Ethyl (phenyl) l-thio-β-d-gluco- and galacto-pyranosides having non-participating (benzyloxy) protecting groups were used as the donors. The αβ-ratio of the products depended on the promoter and conditions of reaction. Intimate ion-pairs, formed initially, may be responsible for the steric outcome of the glycosylations. Thus, with ethyl 2,3,4,6-tetra-O-benzyl-α-d-mannopyranoside as a donor, moderate quantities of the β-linked disaccharide could be produced using MSB as the activator. The synthesis of the title trisaccharide glycoside that contains 1,2-cis and 1,2-trans-linkages is described.

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