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

TitleFacile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors
Publication TypeJournal Article
Year of Publication2011
AuthorsShaikh, AY, Sureshkumar, G, Pati, D, Gupta, SSen, Hotha, S
JournalOrganic & Biomolecular Chemistry
Volume9
Issue17
Pagination5951-5959
Date PublishedMAR
ISSN1477-0520
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.

DOI10.1039/c1ob05056g
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.85
Divison category: 
Organic Chemistry