1,2:5,6-Di-O-isopropylidene-3-C-methyl-α-D-allofuranose

Luana Da Silva Magalhães Forezi,Fernanda Da Costa Santos,Vitor Francisco Ferreira,Marcos Moitrel Pequeno Silva,Maria Cecília Bastos Vieira De Souza

doi:10.1107/s1600536813022447

Luana Da Silva Magalhães Forezi, Fernanda Da Costa Santos + Show 3 more

Open Access

https://doi.org/10.1107/s1600536813022447

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Abstract

The title carbohydrate, C13H22O6, is a derivative of d-glycose, in which the furanosidic and isopropylidene rings are in twisted conformations. The mean plane of the furanosidic ring makes a dihedral angle of 70.32 (18)° with the mean plane of the fused isopropylidene ring. The methyl groups in the other isopropylidene ring are disordered over two sets of sites, with an occupancy ratio of 0.74 (6):0.26 (6). In the crystal, molecules are linked by O—H⋯O hydrogen bonds into chains with graph-set notation C(5) along [100]. Weak C—H⋯O interactions also occur.

Highlights

The title carbohydrate, C13H22O6, is a derivative of d-glycose, in which the furanosidic and isopropylidene rings are in twisted conformations
The methyl groups in the other isopropylidene ring are disordered over two sets of sites, with an occupancy ratio of 0.74 (6):0.26 (6)
As ongoing research in developing potentially new drugs, we report here the structure of 1,2:5,6-Di-O-isopropylidene-3-C-methyl-α-D-allofuranose

Summary

Nonius KappaCCD diffractometer

Absolute structure: Flack x calculated using 872 quotients [(I +) (I )]/[(I +) + (I )]. (Parsons & Flack, 2004). H-atom parameters constrained max = 0.21 e Å3 a Departamento de Quımica Orgânica, Instituto de Quımica, Universidade Federal. Inorgânica, Instituto de Quımica, Universidade Federal Fluminense, Niterói – RJ, CEP 24020-150, Brazil. Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.007 Å; disorder in main residue; R factor = 0.046; wR factor = 0.130; data-to-parameter ratio = 15.2. The title carbohydrate, C13H22O6, is a derivative of d-glycose, in which the furanosidic and isopropylidene rings are in twisted conformations. The methyl groups in the other isopropylidene ring are disordered over two sets of sites, with an occupancy ratio of 0.74 (6):0.26 (6). Data collection: COLLECT (Nonius, 2004); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012)

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