Reaction of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iododemercuriation stereoselectivity affords the alpha-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group, treatment of the iodide with triethylphosphite to afford the corresponding phosphonate, deprotection of the hydroxy group, oxidation, oximation, catalytic hydrogenation and acetylation, afford the phosphono analogue of N-acetyl-alpha-D-mannosamine 1-phosphate.
FIRST SYNTHESIS OF THE PHOSPHONO ANALOG OF N-ACETYL-ALPHA-D-MANNOSAMINE 1-PHOSPHATE / L. CIPOLLA, L. LAY, F. NICOTRA, L. PANZA, G. RUSSO. - In: JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS. - ISSN 0022-4936. - :19(1995), pp. 1993-1994.
FIRST SYNTHESIS OF THE PHOSPHONO ANALOG OF N-ACETYL-ALPHA-D-MANNOSAMINE 1-PHOSPHATE
L. LAYSecondo
;
1995
Abstract
Reaction of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iododemercuriation stereoselectivity affords the alpha-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group, treatment of the iodide with triethylphosphite to afford the corresponding phosphonate, deprotection of the hydroxy group, oxidation, oximation, catalytic hydrogenation and acetylation, afford the phosphono analogue of N-acetyl-alpha-D-mannosamine 1-phosphate.
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