A-D-Glucopyranosyl fluoride

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. 

On treatment of tri-O-acetyl-D-glucal with chlorine and silver fluoride,198 all four possible isomers were formed tri-0-acetyl-2-chloro-2-deoxy-a-D-mannopyranosyl fluoride (16%), tri-0-acetyl-2-chloro-2-deoxy-/3-D-mannopyranosyl fluoride (16%), tri-0-acetyl-2-chloro-2-deoxy-a-D-glucopyranosyl fluoride (6%), and tri-O-acetyl-2-chloro-2-deoxy-/3-D-glucopyranosyl fluoride (62%). These product ratios differ significantly from those of the corresponding bromofluorination and iodofluorination reactions of tri-O -ace tyl-D-glucal,43,53 and this behavior has been discussed198 in terms of the differences observed between the addition of bromine (or iodine) and chlorine to tri-O-acetyl-D-glu-cal, and the nature of the chlorination reaction itself. 

A small piece of Na was added to MeOH (5 mL) and the resulting solution was added to tetra-O-acetyl-a-D-glucopyranosyl fluoride (130 mg, 0.37 mmol) and 4,6-di-6>-acetyl-2-deoxy-2-fluoro-3-0-(tetra-6>-acetyl-/3-D-glucopyranosyl)-/ -D-glucosyl fluoride (44 mg, 0.07 mmol) in MeOH (5 mL) and the solution stirred (1 h) before being neutralized with Amberlite resin IR-120 (H+), fdtered and concentrated to afford a colourless residue. 

Tetra-O-acetyl-a-D-glucopyranosyl Fluoride Typical Procedure 299... 

Tetra-O-benzyl-a-D-glucopyranosyl Fluoride (4) Typical Procedure 41... 

Figure 5. Effect of the substituent group at position C-l on the stimulatory ability of D-glucopyranose. Responses are relative to the maximum sucrose response. Methyl a-o-glucopyranoside (A)> a-D-glucopyranosyl fluoride (A), a-d-glucopyranose (O), l,5-anhydro-D-glucitol(9) (13).

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