Process for preparation of β-glycoside compounds

摘要

The invention provides a process for producing a β-glycoside compound represented by formula (3), characterized in that the process includes causing to react a cyclic alkene compound represented by formula (1) or (2) with a nucleophile in the presence of a transition metal catalyst.;

主权项

1. A process for producing a β-glycoside compound represented by formula (3):wherein R1 represents a halogenated methyl group, an optionally protected formyl group, a C1 to C7 ester group, or an optionally protected hydroxymethylene group; R2 represents an optionally protected hydroxymethylene group, an optionally protected formyl group, a C1 to C7 ester group, a vinyl group, an optionally protected alkynyl group, a cyano group, or an optionally substituted iminomethyl group; X2 represents an oxygen atom; n is 0 or 1; and R3 represents optionally substituted uracil-1-yl, optionally protected thymin-1-yl, optionally protected thymin-3-yl, optionally amino-protected cytosin-1-yl, imidazol-1-yl, benzimidazol-1-yl, benzo-1,2,3-triazol-1-yl, benzo-1,2,3-triazol-2-yl, optionally substituted thiouracil-1-yl, optionally substituted purin-9-yl, C1 to C7 monoalkylamino, C5 to C21 dialkylamino, C1 to C12 alkoxy, optionally substituted phenoxy, C5 to C21 dialkoxycarbonylmethyl, C5 to C21 diacylmethyl, C1 to C7 acyl(alkoxycarbonyl)methyl, C1 to C7 1-nitroalkyl, C1 to C7 1-cyanoalkyl, or C1 to C7 alkylthio,
characterized in that the process comprises causing to react, with a nucleophile in the presence of a transition metal catalyst and a base different from the nucleophile, a glycoside compound represented by formula (1) or formula (2) or formula (4) or formula (5):wherein R1, R2, X2, and n are the same as defined in formula (3), and X1 is an active group selected from the group consisting of alkylcarbonyloxy groups, alkoxycarbonyloxy groups, carbamoyloxy groups, phosphoryl groups, and halogen atoms.