TOTAL SYNTHESIS OF SIALOSYLCEREBROSIDE, GM4

Article abstract of DOI:10.1016/0008-6215(87)80182-9

Desribed are total syntheses of O--(2->3)-O-β-D-galactopyranosyl-(1->1)-(2S,3R,4E)-2-N-tetracosanoylsphingenine, O--(2->3)-O-α-D-galactopyranosyl-(1->1)-(2S,3R,4E)-2-N-tetracosanoylsphingenine, O--(2->3)-O-β-D-galactopyranosyl-(1->1)-(2S,3R,4E)-2-N-tetracosanoylsphingenine and O--(2->3)-O-α-D-galactopyranosyl-(1->1)-(2S,3R,4E)-2-N-tetracosanoylsphingenine by using O-3)-2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate and O--(2->3)-2,4,6,tri-O-acetyl-D-galactopyranosyl trichloroacetimidate as key glycosyl donors, and (2S,3R,4E)-3-O-benzoyl-2-N-tetracosanoylsphingenine as a key glycosyl acceptor.