Synthesis of (1-->4)-linked 2-deoxy-2-fluoroglucose oligomers. 1.
[reaction: see text] Thioglycosides of natural monosaccharides are readily converted into their corresponding chlorides by diphenylchlorosulfonium chloride. This reagent can likewise effect the conversion of the more stable 4-chlorophenylthio 2-deoxy-2-fluoroglucose derivatives into chloride glycosyl donors. On the basis of this activation strategy, it was possible to assemble unnatural oligosaccharides composed of 2-fluorodeoxy sugars.
Sugiyama
S
S
Faculty of Pharmacy & Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, Canada T6G 2N8.
Haque
W
W
Diakur
J
J
D002236:Carbohydrate Conformation; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D009844:Oligosaccharides; D003847:Deoxyglucose