214491-30-2

Basic information

• Product Name: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-, phenylmethyl ester
• CAS NO: 214491-30-2
• Molecular Formula: C30H34BNO6
• Molecular Weight: 515.414
• Mol File: 214491-30-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-, phenylmethyl ester(214491-30-2)
• EPA Substance Registry System: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-, phenylmethyl ester(214491-30-2)

Safety Data

• Hazardous Substances Data: 214491-30-2(Hazardous Substances Data)

Upstream product

• 183070-41-9 L-N^α-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester 
• 262603-98-5 Cbz-Tyr(Nf)-OBzl 
• 220400-04-4 N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine 
• 100-39-0 benzyl bromide 
• 5513-40-6 benzyl N-carbobenzyloxy-L-tyrosine 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 257628-00-5 N-benzyloxycarbonyl-4-iodo-L-phenylalanine benzyl ester 

Downstream Products

• 164203-33-2 N-benzyloxycarbonyl-4-borono-L-phenylalanine 
• 76410-58-7 p-borono-L-phenylalanine 
• 866114-96-7 benzyl (S)-2-[(benzyloxycarbonyl)amino]-3-[4-(borono)phenyl]propionate 

Relevant articles and documents

A practical method for the synthesis of enantiomerically pure 4-borono- L-phenylalanine

Enantiomerically pure L-BPA (4-borono-L-phenylalanine) was synthesized from L-tyrosine or 4-iodo-L-phenylalanine derivatives using the palladium- catalyzed cross-coupling reaction of pinacolborane (2,3-dimethyl-2,3- butanediolatoboron). Cbz-Tyr(Nf)-OBzl (2b) underwent the cross-coupling reaction with pinacolborane (1) in the presence of [PdCl2(PPh3)2] catalyst to give N-benzyloxycarbonyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L- phenylalanine benzyl ester (3a) in 58% yield. The reaction of the 4-iodo-L- phenylalanine derivatives, such as N-benzyloxycarbonyl-4-iodo-L-phenylalanine benzyl ester (2c), N,N-dibenzyl-4-iodo-L-phenylalanine benzyl ester (2d), (4S)-3-benzyloxycarbonyl-4-(4-iodobenzyl)-5-oxazolidinone (2e), and (4S)-3-t- butyloxycarbonyl-4-(4-iodobenzyl)-5-oxazolidinone (2f), with 1 proceeded very smoothly in the presence of [PdCl2(dppf)] catalyst, giving N- benzyloxycarbonyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L-phenylalanine benzyl ester (3a), N,N-dibenzyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L- phenylalanine benzyl ester (3b), (4S)-3-benzyloxycarbonyl-4-[4-(2,3-dimethyl- 2,3-butanediolatoboryl)benzyl]-5-oxazolidinone (3c), and (4S)-3- butyloxycarbonyl-4-[4(2,3-dimethyl-2,3-butanediolatoboryl)benzyl]-5- oxazolidinone (3d), respectively, in high yields. Deprotection of 3a-d gave enantiomerically pure L-BPA in high total yields.