PURPOSE: To enable mass-production of the subject compound which is useful in the metabolic study of catechol estrogen in high yield at low costs by glycosylation of 2-acetyl-estrogen followed by Bayer-Villiger oxidation and deprotection of the product.
CONSTITUTION: The glycosylation of 2-acetylestrogen of formula I (R1 is acetoxyl; R2 is H, ethynyl; R1 and R2 are incorporated into O; R3 is H, acetoxyl; Ac is acetyl) gives 2-acetylestrogen 3-glucoside of formula II (R4 is a glycosyl protecting a functional group), which is subjected to Bayer-Villiger oxidation into 2-acetoxyestrogen 3-glycoside followed by deprotection into the objective 2-hydroxyestrogen 3-glycoside of formula IV (R5 is glycosyl; R6 is hydroxyl; R7 is H, ethynyl; R6, R7 are incorporated into O; R8 is H, hydroxyl).
YUKIMURA SADAAKI
OISHI SHIGEKO
YAGI KUNIO
