SYNTHESIS AND STRUCTURES OF 1,2-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE-3,6-O-CYCLOPHOSPHATE, -THIONO-AND -SELENONOPHOSPHATES

N. S. Magomedova Physico-Chemical Res, Institute by L. Ya. Karpov, ul. Obukha, 10, Moscow, 103064USSR

A. N. Sobolev Physico-Chemical Res, Institute by L. Ya. Karpov, ul. Obukha, 10, Moscow, 103064USSR

V. K. Bel'skii Physico-Chemical Res, Institute by L. Ya. Karpov, ul. Obukha, 10, Moscow, 103064USSR

M. P. Koroteev Physico-Chemical Res, Institute by L. Ya. Karpov, ul. Obukha, 10, Moscow, 103064USSR; Chemistry Department of Moscow, State Pedagogical Institute, Nesvizsky per. 3, Moscow, 119021USSR

N. M. Pugashova Physico-Chemical Res, Institute by L. Ya. Karpov, ul. Obukha, 10, Moscow, 103064USSR; Chemistry Department of Moscow, State Pedagogical Institute, Nesvizsky per. 3, Moscow, 119021USSR

E. E. Nifant'ev Physico-Chemical Res, Institute by L. Ya. Karpov, ul. Obukha, 10, Moscow, 103064USSR; Chemistry Department of Moscow, State Pedagogical Institute, Nesvizsky per. 3, Moscow, 119021USSR

Abstract

3,5,6-Bicyclophosphate of 1,2-O-isopropylidene-α-D-glucofuranose (I), its thiono (II) and selenono (III) analogs undergo unprecedentedly feasible hydrolysis to afford the corresponding 1,2-isopropylidene-α-D-glucofuranose-3,6-cyclophosphate (IV), -thionophosphate (V) and -selenonophosphate (VI). The process is regio- and stereospecific. It occurs with retention of glucose configuration of the monosaccharide backbone and the formation of the phosphepane rings. X-ray structural analysis of the monocyclophosphates formed has been carried out.

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SYNTHESIS AND STRUCTURES OF 1,2-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE-3,6-O-CYCLOPHOSPHATE, -THIONO-AND -SELENONOPHOSPHATES

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SYNTHESIS AND STRUCTURES OF 1,2-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE-3,6-O-CYCLOPHOSPHATE, -THIONO-AND -SELENONOPHOSPHATES

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