Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 17, Pages 5951-5959Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob05056g
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Funding
- CSIR-New Delhi
- DST, New Delhi
- NCL for the LC-MS facility
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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 angstrom 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.
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