Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors
Title | Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors |
Publication Type | Journal Article |
Year of Publication | 2011 |
Authors | Shaikh, AY, Sureshkumar, G, Pati, D, Gupta, SSen, Hotha, S |
Journal | Organic & Biomolecular Chemistry |
Volume | 9 |
Issue | 17 |
Pagination | 5951-5959 |
Date Published | MAR |
ISSN | 1477-0520 |
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-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. |
DOI | 10.1039/c1ob05056g |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 3.85 |
Divison category:
Organic Chemistry