Synthetic studies on glycosphingolipids from protostomia phyla: Synthesis of amphoteric glycolipid analogues containing a phosphocholine residue fromthe earthworm Pheretima hilgendorfi

Two kinds of amphoteric glycosphingolipid analogues from the earthworm Pher etima hilgendorfi were synthesized as follows: The key reaction is a coupli ng of a phosphocholine group at the position C-6 of 1 and 6 which was attem pted using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by reaction of t he resulting cyclic phosphate intermediate with anhydrous trimethylamine to give 2 and 7. Subsequent debenzylation afforded target compounds (3, 8). T heir ability to inhibit the histamine release in vitro was examined.