Abstract
In the title compound C8H14O5, the pento-furan-ose five-membered ring has a twisted conformation on two carbon atoms while the five-membered ring of the iso-propyl-idene group has an envelope conformation on an oxygen atom. Hy-droxy groups are involved an infinite network of O-H⋯O hydrogen bonds that leads to the formation of a layer parallel to the (001) plane. Only weak C-H⋯O contacts exist between neighboring layers.
Highlights
In the title compound C8H14O5, 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
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)
Summary
The title compound, C8H14O5, (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. The reduction proceeded with a total stereoselection from the more accessible Re ( ) side to furnish 1,2-O-isopropylidene-5-O–t-butyldiphenylsilyl- -d-lyxo-furanose, whose desilylation gave the target 1. In the title compound (Fig. 1), the pentofuranose five-membered ring has twisted conformation on atoms C6 and C9 [Q = 0.3175 (12) A , ’ = 117.6 (2)]. The fivemembered ring of the isopropylidene group has an envelope conformation on atom O1 [Q(2) = 0.3192 (11) A , ’ = 187.1 (2)]. 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)
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