Synthesis of a novel series of 4-O-phosphono-D-glucosamine derivatives (lipid A subunit analogs) carrying the C-branched 2-tetradecylhexadecanoyl group

Article abstract of DOI:10.1016/0008-6215(91)80013-D

A novel series of 4-O-phosphono-D-glucosamine derivatives (lipid A subunit analogs) carrying the 3-O-linked or 2-N-linked C-branched 2-tetradecylhexadecanoyl group have been synthesized starting from benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside and benzyl 2-amino-6-O-benzyloxymethyl-2-deoxy-4-O-(diphenoxyphosphinyl)-β-D-gluc opyranoside, respectively. Some of the new compounds were potent inducers of phagocytic activity in macrophages and showed antiviral activity against vaccinia virus. A novel series of 4-O-phosphono-D-glucosamine derivatives (lipid A subunit analogs) carrying the 3-O-linked or 2-N-linked C-branched 2-tetradecylhexadecanoyl group have been synthesized starting from benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D- glucopyra- noside and benzyl 2-amino-6-O-benzyloxy-methyl-2-deoxy- 4-O-(diphenoxyphosphinyl)-β -D-glucopyranoside, respectively. Some of the new compounds were potent inducers of phagocytic activity in macrophages and showed antiviral activity against vaccinia virus.