CHIRAL 4-BORONOPHENYLALANINE (BPA) DERIVATIVE AND METHOD FOR PRODUCING SAME, AND METHOD FOR PRODUCING 18F-LABELED BPA USING SAID DERIVATIVE

摘要

Provided are: a novel chiral 4-boronophenylalanine (BPA) derivative; a method for producing the derivative; and a method for producing 18F-2-fluoro-4-borono-L-phenylalanine (18F-labeled BPA; 18F-BPA) using the derivative. A compound represented by formula (1) is prepared. In the formula, R represents BR3R4, BX3 - or BX3 -M+ (wherein X represents a halogen atom, and M+ represents a monovalent monoatomic cation, a polyatomic cation or a complex cation); R1 represents a hydrogen atom or a protecting group PG1; R2 represents a hydrogen atom or a protecting group PG2; R3 and R4 independently represent OH, or R3, R4 and B together form a ring that serves as a protecting group; and Y represents a halogen atom, NO2, NH2, Sn(R6)3, N=N-NR7R8, OSO2R9, NR10R11, a substituted or unsubstituted phenyliodo group or a substituted or unsubstituted heterocyclic iodo group (wherein R6 represents an alkyl group having 1 to 7 carbon atoms, R7 and R8 may be the same as or different from each other, and independently represent a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms which is substituted by a halogen atom or an optionally substituted phenyl group or R7, R8 and N together form a 3- to 7-membered cyclic structure, R9 represents an alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms which is substituted by a halogen atom, or an optionally substituted phenyl group, and R10 and R11 may be the same as or different from each other, and independently represent an alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms which is substituted by a halogen atom, or an optionally substituted phenyl group or R10, R11 and N together form a 3- to 7-membered cyclic structure, wherein when Y is F, a case in which each of R1 and R2 represents a hydrogen atom and each of R3 and R4 represents OH is excluded). The compound is reacted with a fluorination reagent to prepare 18F-labeled BPA.