Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst | Zendy

Sandra Medina | Zendy; Matthew J. Harper | Zendy; Edward I. Balmond | Zendy; Silvia Miranda | Zendy; Giacomo E. M. Crisenza | Zendy; Diane M. Coe | Zendy; Eoghan M. McGarrigle | Zendy; M. Carmen Galán | Zendy

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Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

Author(s) -

Sandra Medina,

Matthew J. Harper,

Edward I. Balmond,

Silvia Miranda,

Giacomo E. M. Crisenza,

Diane M. Coe,

Eoghan M. McGarrigle,

M. Carmen Galán

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b01962

Subject(s) - chemistry , bifunctional , glycosylation , stereoselectivity , thiourea , organocatalysis , catalysis , organic chemistry , cinchona , combinatorial chemistry , glycoside , enantioselective synthesis , biochemistry

The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.

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