649768-14-9

Upstream product

• 1053637-65-2 (S)-2-(Benzhydrylidene-amino)-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-pent-4-enoic acid tert-butyl ester 
• 1053695-02-5 (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-iodomethyl-allyl)-tetrahydro-pyran 
• 185334-55-8 (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-chloromethyl-allyl)-tetrahydro-pyran 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 501-53-1 benzyl chloroformate 

Relevant academic research and scientific papers

Stereoselective approach to C-glycosylasparagines

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.