Glucopyranosyl fluoride donors

Trialkylsilane resin (PS-DES) 50 was incorporated for solid-phase glycosylation by anchoring a glycosyl donor via their corresponding thio-phenyl ether or 3-glucopyranosyl fluorides (Scheme 20) [59]. Disaccharides... 

W. R. Figures and J. R. Edwards, a-D-Glucopyranosyl fluoride as a D-glucopyr-anosyl donor for a glycosyltransferase complex from Streptococcus mutans FA1, Carbohydr. Res., 48 (1976) 245-253. 

Early on [84,85] it could be demonstrated that glycosyl fluorides were excellent donor substrates for glycosidases [86]. In an example immobilized a-glucosidase (EC 3.2.1.20) could be used for self transfer of a-glucopyranosyl fluoride to give isomaltose (6%), a-isomaltosyl fluoride (25%), and the trisaccharide panose (6%) [87] (O Scheme 14). 

Besides the bromo and chloro functions as the anomeric leaving group, several other glycosyl donors have been utilized. For example, )8-glucopyranosyl fluoride was employed in the total synthesis of apramycin 48 and saccharocin (KA-5685) 49... 

Based on prior experiences where immobilized cyclodextrin a 1-4 glucosyltransferase (iCGT) was prepared and used with a-D-glucopyranosyl fluoride (GF) as the donor (7), we have demonstrated the iCGT catalyzed incorporation of a-D-glucopyranosyl units (G) to polymer-bound maltodextrins (PBM the polymer being water-soluble substituted poly (acrylamide), 8). It has been predicted that using a soluble polymer... 

Glycosylation using a glycosyl fluoride donor activation of 2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl fluoride with a combination of bis-cyclopentadienyl hafnium dichloride (Cp2HfCl2) and silver perchlorate (AgC104). 

Blanchard N, Roush WR. 2-Deoxy-2-iodo-p-glucopyranosyl fluorides mild and highly stereoselective gjycosyl donors for the synthesis of 2-deoxy-p-glycosides from p-hydroxy ketones. Org. Lett. 2003 5 81 4. 

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