1,2-O-Isopropylidene-β-d-lyxo-furanose

In the title compound, the pentofuranose ring has a twisted conformation while the other five-membered ring has an envelope conformation; the two hydroxy groups C are involved in an infinite network of O—H⋯ O bonds, forming a layer parallel to the (001) plane.

In the title compound C 8 H 14 O 5 , the pentofuranose five-membered ring has a twisted conformation on two carbon atoms while the five-membered ring of the isopropylidene group has an envelope conformation on an oxygen atom. Hydroxy groups are involved an infinite network of O-HÁ Á ÁO hydrogen bonds that leads to the formation of a layer parallel to the (001) plane. Only weak C-HÁ Á ÁO contacts exist between neighboring layers.

Structure description
The title compound, C 8 H 14 O 5 , (1) together with its enantiomeric L form, are relatively rare derivatives and a limited volume of information is available for either of them. Our interest in 1 stems from the possibility of conducting deoxygenation at its C3 position to obtain 3-deoxy-1,2-O-isopropylidene--d-threo-pentofuranose as a chiral synthon for further synthetic work (Soares et al., 2013). Compound 1 was obtained from the known 1,2-O-isopropylidene-5-O-t-butyldiphenylsilyl--d-arabino-furanose 2 (Dahlman et al., 1986) via oxidation at the C3 position followed by reduction of the intermediate ulose.
In the crystal, the two hydroxy groups form an infinite network of O-HÁ Á ÁO hydrogen bonds that leads to the formation of a layer parallel to the (001) plane (Table 1, Fig. 2).

Figure 2
Packing diagram of the title compound; view along [100] vector. Highlighted are the layers of molecules connected via O-HÁ Á ÁO hydrogen bonds.

Figure 3
Detail view of the intermolecular C-HÁ Á ÁO interactions.

Figure 1
The title compound with the atom-numbering scheme and 50% probability displacement ellipsoids

Synthesis and crystallization
The synthesis of the title compound is described in Kuzuhara et al. (1971) and Soares et al. (2013).

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. An additional dataset was collected using Cu K radiation, resulting in a Flack parameter of 0.09 (13) and a probability of the absolute configuration being correct of 1.000.

Funding information
Financial support from the State University of New York for the acquisition and maintenance of the X-ray diffractometer is gratefully acknowledged.

data-1
IUCrData ( Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. All hydrogen atoms are refined in isotropic approximation.