Wm. Best et al., ALL ABOUT TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOSYL TRICHLOROACETIMIDATE, Australian Journal of Chemistry, 47(3), 1994, pp. 433-440
Treatment of l-2-(o-carboxybenzoylamino)-2-deoxy-beta-D-glucose with e
thyl chloroformate, followed by workup and treatment with methanol, di
d not give etra-0-acetyl-2-deoxy-2-phthalimido-beta-D-glucose as repor
ted in the literature, but rather the methyl ester -2-(o-methoxycarbon
ylbenzoylamino)-beta-D-glucose. The formation of this methyl ester- is
believed to proceed via ydroisobenzofuran-1'-ylidene)amino]-beta-D-gl
ucose which was also formed from the amido carboxylic acid by treatmen
t with dicyclohexylcarbodiimide. Optimal procedures are given for the
preparation of the title compound tri-O-acetyl-2-deoxy-2-phthalimido-b
eta-D-glucosyl trichloroacetimidate.