Premium
Efficient and Stereoselective Synthesis of α(2→9) Oligosialic Acids: From Monomers to Dodecamers
Author(s) -
Chu KuoChing,
Ren ChienTai,
Lu ChunPing,
Hsu CheHsiung,
Sun TsungHsien,
Han JengLiang,
Pal Bikash,
Chao TsungAn,
Lin YungFeng,
Wu ShihHsiung,
Wong ChiHuey,
Wu ChungYi
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201101794
Subject(s) - stereoselectivity , combinatorial chemistry , monomer , chemistry , glycosylation , block (permutation group theory) , protecting group , stereochemistry , computer science , organic chemistry , mathematics , biochemistry , combinatorics , polymer , alkyl , catalysis
The chain gang : The α(2→9) dodecasialic acid has been stereoselectively synthesized in 12 steps by using a convergent block synthesis (see scheme). The use of chloroacetyl protecting groups and a phosphate group as a leaving group led to the improvement of the α selectivity of the glycosylation reactions, thus allowing synthesis of oligomers.