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Acetobromo-α-D-glucose acts as an intermediate in the preparation of beta-glucosides. It is also used as a possible poly(ethylene terephthalate) surface modification reagent to enhance its blood compatibility.
Glycosyl isothiocyanates have been prepared in good yield by heating fully O-acetylated glycosyl bromides with KSCN in the absence of solvent. With acetobromo-ɑ-D-glucose, displacement was accompanied by stereochemical inversion: Synthesis, 1228 (1995).
Reaction with Bis(cyclopentadienyl)titanium dichloride, A11456 results in 1,2-elimination providing a convenient route to the glycal: J. Org. Chem., 60, 7055 (1995).
Forget, S. M.; Jee, A.; Smithen, D. A.; Jagdhane, R.; Anjum, S.; Beaton, S. A.; Palmer, D. R. J.; Syvitski, R. T.; Jakeman, D. L. Kinetic evaluation of glucose 1-phosphate analogues with a thymidylyltransferase using a continuous coupled enzyme assay. Org. Biomol. Chem. 2015, 13 (3), 866-875.
Xu, Y.; Wang, W.; Cai, Y.; Yang, X.; Wang, P. G.; Zhao, W. A convenient and efficient synthesis of glycals by zinc nanoparticles. RSC Adv. 2014, 4 (87), 46662-46665.