A stereochemical investigation of the cyclisation of D-glucose-6[(R)-16O,17O,18O]phosphate and adenosine-5′[(R)-16O,17O,18O]phosphate

Abstract

D-Glucose-6[(R)-¹⁶O,¹⁷O,¹⁸O] phosphate and adenosine-5′[(R)-¹⁶O,¹⁷O,¹⁸O] phosphate were synthesised and converted (by treatment with diphenyl phosphorochloridate, followed by potassium t-butoxide) into the cyclic 4,6-phosphate and 3′5′-phosphate diesters respectively with retention of configuration at phosphorus; the absolute configuration of D-glucose-6[¹⁶O,¹⁷O,¹⁸O]phosphate and adenosine-5′[¹⁶O,¹⁷O,¹⁸O]phosphate of unknown chirality at phosphorus can now be determined by ³¹P n.m.r. spectroscopy.