Wydział Chemii

Katarzyna Ślepokura

2008

Carbohydrate Research

343

113-131

10.1016/j.carres.2007.09.011

Naukowa

Angielski

Artykuł

The six-membered cyclic phosphate diester, 5,5-dimethoxy-2-oxo-1,3,2-dioxaphosphorinane-2-ol, the dimethyl acetal of cyclic dihydroxyacetone phosphate, (MeO)₂cDHAP, was obtained by the isolation of an intermediate in the basic hydrolysis of the cyclic triester derivative. The compound had been isolated in the form of the crystalline cyclohexylammonium (cha) salts: (cha)[(MeO)₂cDHAP]·3H₂O (5a) and (cha)[(MeO)₂cDHAP]·H₂O (5b), which were then converted into the free acid: (H₅O₂)[(MeO)₂cDHAP] (5c) and then into a series of different salts: Na[(MeO)₂cDHAP]·2H₂O (5d), K[(MeO)₂cDHAP]·1.5H₂O (5e), K[(MeO)₂cDHAP]·0.5H₂O (5e′), Ca[(MeO)₂cDHAP]₂·2H₂O (5f), CaK[(MeO)₂cDHAP]₃·2H₂O (5g) and NH₄[(MeO)₂cDHAP] (5h). The synthesis of the compounds, their crystallization and crystal structures determined by X-ray crystallography are described. The most interesting structural feature observed in 5a–g anions in the crystalline state is the chair conformation of the P/O/C/C/C/O 1,3,2-dioxaphosphorinane ring, which is generally not flattened, in contrast to the deformations often observed in the analogous aryl derivatives (also in (MeO)₂cDHAP(Ph); Ślepokura, K.; Lis, T. Acta Crystallogr. Sect. C2004, 60, o315–o317). However, the anion in crystal 5h is disordered and exists in two conformations, 76% of which is the skew, S, conformation, not observed so far in the compounds of related structure.

Cyclic phosphates, cDHAP, Cyclic dihydroxyacetone phosphate dimethyl acetal, atom, Ion, 2-Dioxaphosphorinane ring, X-ray crystal structure

https://doi.org/10.1016/j.carres.2007.09.011

http://www.elsevier.com