Crystal structure of 3-O-benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-yl)-1,2-O-iso-propyl-idene-α-d-erythro-furan-ose

Nikita Semjonovs; Vitalijs Rjabovs; Dmitrijs Stepanovs; Maris Turks

doi:10.1107/S2056989015022434

Crystal structure of 3-O-benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-yl)-1,2-O-iso-propyl-idene-α-d-erythro-furan-ose

Acta Crystallogr E Crystallogr Commun. 2015 Nov 28;71(Pt 12):1542-4. doi: 10.1107/S2056989015022434. eCollection 2015 Dec 1.

Authors

Nikita Semjonovs¹, Vitalijs Rjabovs¹, Dmitrijs Stepanovs², Maris Turks¹

Affiliations

¹ Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena 3/7, Riga, LV-1048, Latvia.
² Latvian Institute of Organic Synthesis, Str. Aizkraukles 21, Riga, LV 1006, Latvia.

Abstract

The title compound, C23H25N3O4, {systematic name: 1-benzyl-4-[(3aR,5R,6R,6aR)-6-benz-yloxy-2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxol-5-yl]-1H-1,2,3-triazole}, consists of a substituted 2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxole. The furan-ose ring adopts an envelope conformation close to C 3-exo, where the C atom substituted by the benz-yloxy group is the flap. The fused dioxolane ring also adopts an envelope conformation, with the methyl-ene C atom as the flap. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming zigzag chains along [010].

Keywords: 1,2,3-triazole; carbohydrate triazole conjugate; click chemistry; crystal structure; pseudo-nucleoside.