TY - JOUR T1 - Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors JF - Organic & Biomolecular Chemistry Y1 - 2011 A1 - Shaikh, Ashif Y. A1 - Sureshkumar, Gopalsamy A1 - Pati, Debasish A1 - Sen Gupta, Sayam A1 - Hotha, Srinivas AB -

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-trans glycosides in good yields under AuBr(3)/4 angstrom MS Powder/CH(2)Cl(2)/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.

PB - ROYAL SOC CHEMISTRY CY - THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND VL - 9 IS - 17 U3 - Foreign U4 - 3.85 ER -