@article{a797f416f9354ba892c3d513ad371b9d,
title = "A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α- galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2- deoxygalactopyranosyl diphenyl phosphates: Stereoselective synthesis of mucin core 5 and core 7 structures",
abstract = "TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2- deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et 2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of α-selectivity (α/β=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.",
keywords = "Carbohydrates, Glycosylation, Mucin, Phosphates, T -antigen",
author = "Kosuke Kakita and Toshifumi Tsuda and Noritoshi Suzuki and Seiichi Nakamura and Hisanori Nambu and Shunichi Hashimoto",
note = "Funding Information: This research was supported, in part, by a Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Organic Synthesis Based on Reaction Integration{\textquoteright} (No. 2105) from the Ministry of Education, Culture, Sports, Science and Technology , Japan. We thank Ms. S. Oka, and M. Kiuchi of the Center for Instrumental Analysis at Hokkaido University for technical assistance in the MS and elemental analyses.",
year = "2012",
month = jun,
day = "24",
doi = "10.1016/j.tet.2012.04.059",
language = "英語",
volume = "68",
pages = "5005--5017",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Ltd.",
number = "25",
}