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Study of Hydroxypiperidine Radical Rearrangement
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1-deoxynojirimycin 50 uL aliquot a-Glucosidase by 65 acid active site Add 50 uL added afford alcohol almond P-glucosidase amine aromatics assays azaoligosaccharides azasugars benzyl binding buffer to tube Carbohydr catalyst cellulase CH2OH CH3OH CHCI3 Chem chlorohydrin chromatographed through silica CIMS concentration deionized water deprotection disaccharide dried epoxide epoxide 65 equiv ether evaporated to dryness exoglycosidases extracted with CH2CI2 filtered fusca glucose glycine glycine buffer glycosidases glycosidic glycosidic bond H-NMR CDCI3 HBF4 hexane:EtOAc Hr or Hr hydrolysis hydroxyl Inactivation of Almond Inactivation of Yeast inhibition inhibitors IR(film lysozyme m/e relative intensity methanol mixture was stirred mL of glycine mmol NMR CDCI3 nucleophilic OCH2Ph oligosaccharides orthoester Ph2CH3P PhCHN2 phenyldiazomethane piperidine preincubation pyridine pyrrolidines reaction was stirred resulting solution room temperature Scheme solution to 50 stilbenes stirred at room substrate solution synthesis trichloroacetimidate uL of substrate vacuo Yeast a-Glucosidase yield