Crystal structure of (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-methoxy-3-phenyl-2,5-dihydrofuran-2-one

Abstract

In the title compound, C13H14O5, the furan ring is essentially planar [maximum deviation = 0.031 (3) Å] with a stereogenic center (R) at thesp3hybridized C atom. The C atom bearing the dihydroxy ethyl group isS. The absolute configuration is based on the precursor in the synthesis. The two O—H groups are in ananticonformation with respect to each other. The mean plane of the furanone group is twisted by 8.2 (4)° from that of the phenyl ring. In the crystal, molecules are linked by O—H...O hydrogen bonds involving furanone C=O groups and symmetry-related hydroxy groups, forming a two-dimensional network parallel to (001). Weak C—H...O hydrogen bonds are observed within the two-dimensional network.