PRODUCTION OF PHENYL-ALPHA-GLYCOSIDE DERIVATIVE

摘要

PURPOSE: To obtain a phenyl-α-glycoside derivative useful as a substrate for measuring activity of glucosidase in high yield by reacting a 1-hydroxy derivative of a saccharide with 3-chloro-4-fluoronitrobenzene in the presence of a base in an aprotic polar solvent. CONSTITUTION: A 1-hydroxy derivative of a saccharide of formula I (Ac is acetyl; wavy line shows α or β configuration) or formula II ((m) is an integer of 0-5) (e.g. 1-hydroxy-heptaacetylmaltose) is reacted with 3-chloro-4- fluoronitrobenzene in the presence of an organic base (e.g. 1,8- diazabicyclo[5.4.0]-7-undecene) in an aprotic polar solvent (e.g. hexamethyl phosphoric acid triamide) as a reaction solvent to give the objective phenyl-α- glycoside derivative of formula III ((n) is an integer of 0-6) useful as a synthetic intermediate for a substrate for measuring activity of glycosidase and amylase in high yield.