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.