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
