Fragments of biopolymers containing glycosyl phosphate residues. 7. 31P NMR studies on the reaction of glycosyl hydrogenphosphonates with trimethylacetyl chloride and alcohols
A. V. Nikolaev, I. A. Ivanova, V. N. Shibaev, A. V. Ignatenko
N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: Interaction of glycosyl H-phosphonates and Me3CCOCl was studied with 31P NMR spectroscopy in pyridine and quinoline solutions. It was shown to lead to the mixed anhydrides and diacyl phosphites, which were converted into the H-phosphonate diesters and the phosphite triesters after addition of alcohol. The diesters reacted slowly with Me3CCOCl and ethanol to form the phosphite triesters and the C-phosphonate diesters. The glycosyl diethyl phosphite triester in pyridine solution was converted slowly into diet-hyl H-phosphonate. Possible reaction pathways of glycosyl H-phosphonates and the intermediates are discussed.
Russian Journal of Bioorganic Chemistry 1991, 17 (11):1550-1561