THE PHTHALATION OF 2-AMINO-2-DEOXY-D-GLUCOSE AND N-METHYL-1-AMINO-1-DEOXY-D-GLUCITOL; CONVERSION OF THE PRODUCTS TO ORGANOTIN DERIVATIVES. A READY MIGRATION OF ACETYL FROM OXYGEN TO NITROGEN UNDER NEUTRAL CONDITIONS

Article abstract of DOI:10.1002/recl.19881070315

N-Phthalation of 3-amino-3-deoxy-D-glucose was followed by replacement of the acidic proton by tributyl- and triphenylstannyl groups.A similar reaction with 1-(methylamino)-1-deoxy-D-glucitol failed and successive treatment with benzyl chloroformate and acetic anhydride followed by catalytic hydrogenation showed that a 1,4-O->N acetyl migration had occured.Phthalation and stannylation succeeded under different conditions.