A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-alpha-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures

作者：Kakita Kosuke; Tsuda Toshifumi; Suzuki Noritoshi; Nakamura Seiichi; Nambu Hisanori; Hashimoto Shunichi^*

来源：Tetrahedron, 2012, 68(25): 5005-5017.

DOI：10.1016/j.tet.2012.04.059

• Carbohydrates
• Glycosylation
• T-N-antigen
• Mucin
• Phosphates

TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides.

• 出版日期2012-6-24