225663-06-9Relevant academic research and scientific papers
A novel and efficient route towards α-GalNAc-Ser and α-GalNAc-Thr building blocks for glycopeptide synthesis
Winterfeld, Gottfried A.,Ito, Yukishige,Ogawa, Tomoya,Schmidt, Richard R.
, p. 1167 - 1171 (1999)
Michael addition of serine and threonine derivatives 4a-4c to 3,4,6-tri- O-benzyl-2-nitro-D-galactal (1) afforded the corresponding 2-deoxy-2-nitro- α-D-galactopyranosides 5a-5c in good yield and stereoselectivity. 2-deoxy-2- nitroglycosides 5a and 5b were reduced to the 2-acetamido compounds by platinized Raney nickel T4. Manipulation of the protecting groups afforded known N-Fmoc-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D- galactopyranosyl)-L-serine (8a) and -threonine (8b), valuable building blocks for O-glycopeptide synthesis.
