Synthesis and characterization of five phosphates of L-glycero-D-manno-heptose

• Authors: B. Grzeszczyk , A. Zamojski
• Languages of publication: PL

Abstracts

EN

Five monophosphates of L-glycero-D-manno-heptose having the PO(OH)2 residue at O-2,3,4,6 and 7 have been synthesized starting from suitably protected benzyl D-mannopyranoside derivatives. The synthesis involved chain elongation by the reaction of D-mannoside 6-aldehyde with alkoxymethylmagnesium chloride resulting in the desired L-glycero-D-manno-heptopyranoside as the main product. The blocking groups pattern enabled selective deprotection of the hydroxyl groups at C-2, 3, 4, and 7. These substrates were phosphitylated with 2-dimethylamino-5,6-benzo-1,3,2- dioxaphosphepan and oxidized in situ to phosphates. The resulting products were hydrogenolytically deprotected and converted to di(cyclohexylammonium) salts which were characterized by 13C-NMR spectra.

Keywords

EN

HEPTOSE; HEPTOSE-PHOSPHATE; LIPOPOLYSACCHARIDE

Discipline

• EXPERIMENTAL_BIOLOGY_&_MEDICINE: EXPERIMENTAL BIOLOGY & MEDICINE

• Journal: Postępy Higieny i Medycyny Doświadczalnej
• Year: 1996
• Volume: 50
• Issue: 5
• Pages: 483-491

Contributors

author

B. Grzeszczyk

author

A. Zamojski

• Document Type: article
• Publication order reference: B.Grzeszczyk, ul. Malej Laki 13 m. 5, 02-793 Warszawa, Poland