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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.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant