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. Author manuscript; available in PMC: 2010 Oct 1.
Published in final edited form as: Colloids Surf B Biointerfaces. 2009 May 5;73(1):65–74. doi: 10.1016/j.colsurfb.2009.04.023

Scheme 1.

Scheme 1

Synthesis and chemical structure of perfluoroalkyl and alkyl glycosides. (a. DMAP, Ac-Cl, pyridine, DCM; b. F(CF2)mI, AIBN; c. HI (55%), Zn, C2H5OH; d. CH3OH, KOH; e. CH3OH, PTSA, toluene; f. F(CF2)mI (m=4,6 or 8), AIBN; g. HI (55%), Zn, C2H5OH; h. LiAlH4, anhydrous ether, ambient temperature; i. BF3/OEt2 (48%), anhydrous DCM (α-anomer: 0°C for 20 min, then 30°C for 10h; β-anomer: 0°C for 2h, then warmed to ambient temperature); j. MeONa/MeOH, 0°C to ambient temperature; k. Dowex®50W×8-100 ion-exchange resin).