Bromoacetyl glucose

Formation of 2,3,4,6-tetra-O-acetyl-D-glucopyranose is obtained by treating bromoacetyl glucose in acetone containing silver carbonate [48,49] (reaction 4.48). 

The reaction of bromoacetyl glucose with lithium aluminum hydride in diethyl ether gives the substitution of hydrogen for the hemiacetal hydroxyl at C-1, and the formation of the nonreducing, 1,5-anhydro-D-glucitol [50,51] (reaction 4.49). The excess LiAlH is removed by the addition of ethyl acetate, which is reduced to ethanol. 

The 1-phosphate can be prepared by reaction of bromoacetyl glucose with silver phosphate in benzene or toluene. The anomeric form of the resulting product... 

The reaction of bromoacetyl glucose and bromoacetyl galactose with sodium azide in DMF gives 68 and 75% yields, respectively, of the 1-P-azide [55] (reaction 4.53). The azide can be easily reduced by catalytic hydrogenation to give 1-glycosylamines. 

Reaction of bromoacetyl glucose with trimethylammonium bromide [60,61] or with alkali [62] forms 1,6-anhydro-D-glucopyranoside, commonly called levoglu-cosan (reaction 4.56). 

The 1,2-anhydride is very reactive and has been used to synthesize p-glyco-sidic linkages [63,65,66]. At elevated temperatures (80-100°C) a-glycosidic linkages are formed [64,65]. p-Glycosides are also synthesized from bromoacetyl glucose by the Koenigs-Knorr reaction (see section g.i.). 

The A -bromo-, chloro-, and fluoro-acetyl derivatives of 2-amino-2-deoxy-D-glucose and -o-galactose have been prepared and tested for cytotoxic activity the per-O-acetylated A -bromoacetyl derivatives in either the glucose or galactose series were most effective against Friend erythroleukemia cells. A -nictotinoyl derivatives of 2-amino-2-deoxy-D-glucose and its ethyl a- and j8-pyranoside have been prepared. ... 

Becker et al. specifically inactivated the biotin transport system of E. coli using biotin p-nitrophenyl ester. The lactose transport protein of E. coli was labeled by AT-bromoacetyl-/8-D-galactopyranosylamine. In the only reported attempt to isolate an affinity labeled protein, glucose 6-isothiocyanate, which is an affinity label for the glucose transport system in human erythrocytes, gave enough nonspecific labeling of other membrane proteins to render identification of the transport protein difficult. 

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