Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors†
Ashif Y. Shaikh,Gopalsamy Sureshkumar,Debasish Pati,Sayam Sen Gupta,Srinivas Hotha
Organic & Biomolecular Chemistry Pub Date : 03/09/2011 00:00:00 , DOI:10.1039/C1OB05056G
Abstract

Propargyl 1,2-O-orthoesters are exploited for the synthesis of 1,2-trans O-glycosides of protected amino acids. N-Fmoc- and N-Cbz protected serine/threonine - benzyl/methyl esters reacted well with glucosyl-, galactosyl-, mannosyl- and lactosyl- derived propargyl 1,2-orthoesters affording respective 1,2-transglycosides in good yields under AuBr3/4 Å MS Powder/CH2Cl2/rt. t-Boc serine derivative gave serine 1,2-orthoester and glycosyl carbamate. Optimized conditions enabled preparation of new glycosyl carbamates from N-Boc protected amines in a single step using gold catalysts and propargyl 1,2-orthoesters in excellent yields.

Graphical abstract: Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors