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

doi:10.1039/C1OB05056G

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Organic & Biomolecular Chemistry

Issue 17, 2011

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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 and Srinivas Hotha

Org. Biomol. Chem., 2011,9, 5951-5959

DOI: 10.1039/C1OB05056G
Received 10 Jan 2011, Accepted 09 Mar 2011
First published on the web 09 Mar 2011

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Abstract
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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 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.