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.

Cipolla, L., Lay, L., Nicotra, F., Panza, L., & Russo, G. (1995). FIRST SYNTHESIS OF THE PHOSPHONO ANALOG OF N-ACETYL-ALPHA-D-MANNOSAMINE 1-PHOSPHATE. JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS(19), 1993-1994 [10.1039/c39950001993].

FIRST SYNTHESIS OF THE PHOSPHONO ANALOG OF N-ACETYL-ALPHA-D-MANNOSAMINE 1-PHOSPHATE

CIPOLLA, LAURA FRANCESCA;NICOTRA, FRANCESCO;
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.
Articolo in rivista - Articolo scientifico
glycosyl phosphonates; carbohydrate mimetics; C-glycosides
English
1993
1994
2
Cipolla, L., Lay, L., Nicotra, F., Panza, L., & Russo, G. (1995). FIRST SYNTHESIS OF THE PHOSPHONO ANALOG OF N-ACETYL-ALPHA-D-MANNOSAMINE 1-PHOSPHATE. JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS(19), 1993-1994 [10.1039/c39950001993].
Cipolla, L; Lay, L; Nicotra, F; Panza, L; Russo, G
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/31758
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