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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

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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
Authors: Kakita, Kosuke Browse this author
Tsuda, Toshifumi Browse this author
Suzuki, Noritoshi Browse this author
Nakamura, Seiichi Browse this author
Nambu, Hisanori Browse this author →KAKEN DB
Hashimoto, Shunichi Browse this author →KAKEN DB
Keywords: Carbohydrates
Glycosylation
TN-antigen
Mucin
Phosphates
Issue Date: 24-Jun-2012
Publisher: Elsevier
Journal Title: Tetrahedron
Volume: 68
Issue: 25
Start Page: 5005
End Page: 5017
Publisher DOI: 10.1016/j.tet.2012.04.059
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/Et2O (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.
Type: article (author version)
URI: http://hdl.handle.net/2115/49671
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 南部 寿則

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