1053637-65-2Relevant articles and documents
Stereoselective approach to C-glycosylasparagines
Lygo, Barry,Andrews, Benjamin I.,Slack, Daniel
, p. 9039 - 9041 (2007/10/03)
In this paper we describe a simple and efficient approach to N-glycopeptide analogues that incorporate a ketomethylene unit in place of a native amide link. Key C-C bond forming steps involve the stereocontrolled addition of a functionalised allylsilane to activated sugar derivatives and the asymmetric phase-transfer alkylation of a glycine imine. Utility of this chemistry is demonstrated by the synthesis of a C-analogue of the glycopeptide core found in nephritogenoside. Regioselective ozonolysis of a 1,5-diene is also described.