Step-by-step synthesis of linear pentamannosyltetraphosphate via glycosyl hydrogenphosphonates

A. V. Nikolaev, I. A. Ivanova, V. N. Shibaev

N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

Abstract: Step-by-step synthesis of linear (16)-linked methyl tetra(α-D-mannopyranosyl phosphate)-α-D-mannopyranoside was developed with the use of the hydrogenphospho-nate method. Methyl 2,3,4-tri-O-acetyl-α-D-mannopyranoside served as first acceptor of the oligo(mannosyl phosphate) chain. Elongation cycle included coupling of 2,3,4-tri-O-benzoyl-6-O-dimethoxytrityl-a-D-mannopyranosyl H-phosphonate and a hydro-xyl component in the presence of Me3CCOCl followed by oxidation and detritylation. 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl H-phosphonate was employed in the final step. After complete deprotection the title oligomer was isolated in 30% overall yield.

Russian Journal of Bioorganic Chemistry 1990, 16 (12):1696-1699

Full Text (PDF, in Russian)