THE SYNTHESIS OF FIVE L-GLYCERO-D-MANNO-HEPTOSE MONOPHOSPHATES

摘要

From suitably protected benzyl alpha-D-mannopyranosides, five benzyl L-glycero-alpha-D-mannoheptopyranosides were synthesized by chain-elongation at C-6. By regiospecific protection-deprotection procedures five O-benzylated heptosides having 'isolated' free OH groups at C-2, C-3, C-4, C-6, or C-7 were obtained. These substrates were phosphorylated and the products were converted into free monophosphates or monophosphate cyclohexylammonium salts (1-5) which were characterized by H-1, C-13, and P-31 NMR spectra and high-performance anion-exchange chromatography. (C) 1996 Elsevier Science Ltd. [References: 11]