A novel glycosyl donor for the synthesis of cancer specific Core 5 and sialyl Core 5 as glycopeptide building blocks

Article abstract of DOI:10.1016/S0040-4039(96)02490-2

Trichloroacetimidate at 1 and 3 position of 4,6-benzylidenyl N-acetylgalactosamine serves as a leaving group for glycosylation and a selective and acid sensitive protecting group respectively. This versatile donor, while forming exclusive α-glycoside with serine/threonine, serves as a fascile precursor to 3-OH which can be generated in acid medium without affecting 4,6-acetal protecting group or the protecting groups of serine/threonine. Synthesis of cancer associated carbohydrate Core 5 and its sialylated analog are accomplished through the use of this donor.