4-Borono-L-phenylalanine supplier

Name
4-BORONO-L-PHENYLALANINE
EINECS
CAS No. 76410-58-7
Article Data8
CAS DataBase
Density 1.34 g/cm³
Solubility
Melting Point 285-293oC (dec.)
Formula C₉H₁₂BNO₄
Boiling Point 449.3 °C at 760 mmHg
Molecular Weight 209.01
Flash Point 225.5 °C
Transport Information
Appearance
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 4-Borono-L-phenylalanine;L-BPA;L-p-Boronophenylalanine;4-boronophenylalanine;4-(dihydroxyboranyl)-L-phenylalanine;4-(Dihydroxyboryl)-L-phenylalanine;L-Phenylalanine, 4-borono-;p-Borono-L-phenylalanine;4-Borono-L-phenylalanine B10 enriched;
PSA 103.78000
LogP -0.97890

Synthetic route

: 119771-23-2
N-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-1-phenylalanine

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 55℃; for 1.5h;	93.2%
With hydrogenchloride In water; acetone for 4h; Heating;	70.18%
With sulfuric acid In 1,4-dioxane at 20℃; for 1h; Hydrolysis;	67%

: 262604-05-7
4-borono-N,N-dibenzyl-L-phenylalanine benzyl ester

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In ethanol; water at 60℃; under 3750.38 - 9000.9 Torr; Reagent/catalyst; Temperature; Autoclave;	91%
With hydrogenchloride; hydrogen; palladium dihydroxide In ethanol at 20℃; for 19h; Hydrogenolysis;	44%

: 7732-18-5
water

: 262604-04-6
(4S)-3-t-butyloxycarbonyl-4-[4-(2,3-dimethyl-2,3-butanediolatoboryl)benzyl]-5-oxazolidinone

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
With sodium hydroxide; sodium periodate; sulfuric acid In 1,4-dioxane; water; acetone 1) NaIO4, NH4OAc, acetone/water, room temp., 48 h; 2) aq. NaOH, 1 h; 3)aq. H2SO4, 1,4-dioxane, room temp., 1 h; removal of solvent, neutralization with aq. NaOH;	67%

: 164203-33-2
N-benzyloxycarbonyl-4-borono-L-phenylalanine

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium dihydroxide In ethanol at 20℃; for 19h; Hydrogenolysis;	63%

: 1333-74-0
hydrogen

: 164203-33-2
N-benzyloxycarbonyl-4-borono-L-phenylalanine

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride In ethanol Pd(OH)2/C, room temp., 19 h; filtration, neutralization to pH 7.0 (aq. NaOH), filtration of solid, washing with water;	63%

: 1333-74-0
hydrogen

: 262604-05-7
4-borono-N,N-dibenzyl-L-phenylalanine benzyl ester

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride In ethanol Pd(OH)2/C, room temp., 19 h; filtration, neutralization to pH 7.0 (aq. NaOH), filtration of solid, washing with water;	44%

: 5513-40-6
benzyl N-carbobenzyloxy-L-tyrosine

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 99.8 percent / triethylamine / CH2Cl2 / 28 h / 0 - 20 °C 2: 58 percent / Et3N / [PdCl2(PPh3)2] / dioxane / Heating 3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 4: 207 mg / aq. NaOH / 1 h 5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 1991-81-7, 14173-41-2, 24250-85-9, 62561-75-5
4-iodo-L-phenylalanine

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 57 percent / NaCO3 / H2O / 24 h / 130 °C 2: 84 percent / Et3N / [PdCl2(dppf)] / dioxane / 36 h / 80 °C 3: 81 percent / NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 4: 44 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / 1,4-dioxane; water / 19 °C 1.2: 8 h / 0 - 30 °C 2.1: 1,5-bis(methylamino)-3-oxapentane; tert-butylmagnesium chloride; sodium hydride / mineral oil; tetrahydrofuran / 22.5 h / 0 - 30 °C / Inert atmosphere 3.1: hydrogenchloride / water; acetone / 4 h / Heating View Scheme

: 220400-04-4
N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 97 percent / p-TsOH*H2O / toluene / 3 h / Heating 2: 72 percent / Et3N / [PdCl2(dppf)] / dioxane / 27 h / 80 °C 3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 4: 1.30 g / aq. NaOH / 1 h 5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: 96 percent / Cs2CO3 / methanol; dimethylformamide / 2 h / 20 °C 2: 82 percent / Et3N / [PdCl2(dppf)] / dioxane / 100 °C 3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 4: 207 mg / aq. NaOH / 1 h 5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 183070-41-9
L-Nα-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 5 percent / Et3N / [PdCl2(dppf)] / dioxane / 80 °C 2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 207 mg / aq. NaOH / 1 h 4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 262604-00-2
(4S)-3-benzyloxycarbonyl-4-(4-iodobenzyl)-5-oxazolidinone

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 72 percent / Et3N / [PdCl2(dppf)] / dioxane / 27 h / 80 °C 2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 1.30 g / aq. NaOH / 1 h 4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 286472-74-0
C18H18BNO6

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.30 g / aq. NaOH / 1 h 2: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 257628-00-5
N-benzyloxycarbonyl-4-iodo-L-phenylalanine benzyl ester

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 82 percent / Et3N / [PdCl2(dppf)] / dioxane / 100 °C 2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 207 mg / aq. NaOH / 1 h 4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 262604-03-5
(4S)-3-benzyloxycarbonyl-4-[4-(2,3-dimethyl-2,3-butanediolatoboryl)benzyl]-5-oxazolidinone

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 2: 1.30 g / aq. NaOH / 1 h 3: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 262603-99-6
4-iodo-N,N-dibenzyl-L-phenylalanine benzyl ester

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / Et3N / [PdCl2(dppf)] / dioxane / 36 h / 80 °C 2: 81 percent / NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 44 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: Bis<2-(N,N-dimethylamino)aethyl>aether; isopropylmagnesium chloride / tetrahydrofuran / 0 - 5 °C 1.2: 4 h / -20 °C 2.1: hydrogenchloride 3.1: hydrogenchloride; 5%-palladium/activated carbon; hydrogen / ethanol; water / 60 °C / 3750.38 - 9000.9 Torr / Autoclave View Scheme

: 866114-96-7
benzyl (S)-2-[(benzyloxycarbonyl)amino]-3-[4-(borono)phenyl]propionate

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 207 mg / aq. NaOH / 1 h 2: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 214491-30-2
N-benzyloxycarbonyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L-phenylalanine benzyl ester

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 2: 207 mg / aq. NaOH / 1 h 3: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 262604-02-4
N,N-dibenzyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L-phenylalanine benzyl ester

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 2: 44 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: 262603-98-5
Cbz-Tyr(Nf)-OBzl

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 58 percent / Et3N / [PdCl2(PPh3)2] / dioxane / Heating 2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C 3: 207 mg / aq. NaOH / 1 h 4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C View Scheme

: C22H36BNO6

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / 20 - 25 °C / pH 3 - 4 2: hydrogenchloride / acetone; water / 1.5 h / 55 °C View Scheme

: 103882-09-3, 62129-44-6
N-Boc-4-I-Phe-OH

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: n-butyllithium / 2-methyltetrahydrofuran; hexane / 2.5 h / -85 - -76 °C 2: hydrogenchloride / 20 - 25 °C / pH 3 - 4 3: hydrogenchloride / acetone; water / 1.5 h / 55 °C View Scheme
Multi-step reaction with 2 steps 1: 1,5-bis(methylamino)-3-oxapentane; tert-butylmagnesium chloride; sodium hydride / mineral oil; tetrahydrofuran / 22.5 h / 0 - 30 °C / Inert atmosphere 2: hydrogenchloride / water; acetone / 4 h / Heating View Scheme

: C32H34BNO4

: 76410-58-7
p-borono-L-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride 2: hydrogenchloride; 5%-palladium/activated carbon; hydrogen / ethanol; water / 60 °C / 3750.38 - 9000.9 Torr / Autoclave View Scheme

: 945978-64-3
4-chloro-6-(2,2,2-trifluoro-1-(3'-fluoro-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-2-amine

: 76410-58-7
p-borono-L-phenylalanine

: (2S)-2-amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-(3'-fluoro-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-4-yl)phenyl)propanoic acid

Conditions

Conditions	Yield
Stage #1: 4-chloro-6-(2,2,2-trifluoro-1-(3'-fluoro-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-2-amine; p-borono-L-phenylalanine With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.116667h; Suzuki Coupling; Microwave irradiation; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In diethyl ether; water at 0℃; for 0.5h; pH=6.5;	99%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 150℃; for 0.116667h; Suzuki coupling; Microwave irradiation;

Yield

Stage #1: 4-chloro-6-(2,2,2-trifluoro-1-(3'-fluoro-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-2-amine; p-borono-L-phenylalanine With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.116667h; Suzuki Coupling; Microwave irradiation;
Stage #2: With sodium hydroxide In water
Stage #3: With hydrogenchloride In diethyl ether; water at 0℃; for 0.5h; pH=6.5;

99%

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 150℃; for 0.116667h; Suzuki coupling; Microwave irradiation;

: (211)astatine

: 76410-58-7
p-borono-L-phenylalanine

: 73538-17-7
4-[211At]astato-L-phenylalanine

Conditions

Conditions	Yield
With N-chloro-succinimide; sodium hydrogencarbonate In water at 20℃; for 0.5h; Reagent/catalyst;	95%

: 76410-58-7
p-borono-L-phenylalanine

: L-p-[123I]iodo-phenylalanine

Conditions

Conditions	Yield
With N-Bromosuccinimide; [123I] sodium iodide; sodium hydrogencarbonate; sodium hydroxide In water at 20℃; for 0.5h;	93%

: 76410-58-7
p-borono-L-phenylalanine

: 87-42-3
6-chloropurine

: (S)-3-{4-[9H-purin-6-yl]phenyl}-2-aminopropanoic acid

Conditions

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0833333h; Suzuki-Miyaura cross-coupling; microwave irradiation;	90%

: 76410-58-7
p-borono-L-phenylalanine

: 166247-63-8
7-deaza-2'-deoxy-7-iodoadenosine

: (S)-2-amino-3-{4-[6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-7-deazapurin-7-yl]phenyl}propanoic acid

Conditions

Conditions	Yield
With sodium carbonate; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 100℃; for 1h; Suzuki-Miyaura cross-coupling reaction;	89%

: 76410-58-7
p-borono-L-phenylalanine

: 60-18-4
L-tyrosine

Conditions

Conditions	Yield
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Irradiation;	85%

: 2004-06-0
6-Chloropurine riboside

: 76410-58-7
p-borono-L-phenylalanine

: (S)-3-{4-[9-(β-D-ribofuranosyl)purin-6-yl]phenyl}-2-aminopropanoic acid

Conditions

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0166667h; Suzuki-Miyaura cross-coupling; microwave irradiation;	84%

: 76410-58-7
p-borono-L-phenylalanine

: 6974-78-3
8-bromoadenine

: (S)-2-amino-3-[4-(6-amino-9H-purin-8-yl)phenyl]propanoic acid

Conditions

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0833333h; Suzuki-Miyaura cross-coupling; microwave irradiation;	84%

: 348-52-7
1-Fluoro-2-iodobenzene

: 76410-58-7
p-borono-L-phenylalanine

: (S)-2-Amino-3-(2'-fluoro-biphenyl-4-yl)-propionic acid

Conditions

Conditions	Yield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; Suzuki coupling; Irradiation;	81%

: 64-17-5
ethanol

: 76410-58-7
p-borono-L-phenylalanine

: 77374-24-4
C11H16BNO4*ClH

Conditions

Conditions	Yield
hydrogenchloride	80%

: 54-42-2
5-Iodo-2'-deoxyuridine

: 76410-58-7
p-borono-L-phenylalanine

: (S)-2-amino-3-{4-[1-(2-deoxy-β-D-erythro-pentofuranosyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl}propanoic acid

Conditions

Conditions	Yield
With sodium carbonate; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 100℃; for 1.5h; Suzuki-Miyaura cross-coupling reaction;	78%

: 76410-58-7
p-borono-L-phenylalanine

: 2946-39-6
8-bromoadenosine

: (S)-2-amino-3-{4-[6-amino-9-(β-D-ribofuranosyl)purin-8-yl]phenyl}propanoic acid

Conditions

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0833333h; Suzuki-Miyaura cross-coupling; microwave irradiation;	76%
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In acetonitrile at 90℃; for 2h; Suzuki coupling;	71%

: 76410-58-7
p-borono-L-phenylalanine

: 14985-44-5
8-bromo-2'-deoxyadenosine

: (S)-2-amino-3-{4-[6-amino-9-(2-deoxy-β-D-erythropentafuranosyl)purin-8-yl]phenyl}propanoic acid

Conditions

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In acetonitrile at 90℃; Suzuki coupling;	75%
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 90℃; for 2h; Suzuki-Miyaura cross-coupling;	75%
With sodium carbonate; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 90℃; for 2h; Suzuki-Miyaura cross-coupling reaction;	75%

: 1033805-83-2
4-chloro-6-[R-2,2,2-trifluoro-1-(5-fluoro-2-(3-methylpyrazol-1-yl)phenyl)ethoxy]pyrimidin-2-ylamine

: 76410-58-7
p-borono-L-phenylalanine

: 1033805-80-9
(S)-2-amino-3-[4-(2-amino-6-{(R)-2,2,2-trifluoro-1-[5-fluoro-2-(3-methyl-pyrazol-1-yl)-phenyl]-ethoxy}-pyrimidin-4-yl)-phenyl]-propionic acid

Conditions

Conditions	Yield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 160℃; for 0.166667h; Microwave irradiation;	75%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 160℃; for 0.166667h; Microwave irradiation; Sealed tube;	1.163 g

: 76410-58-7
p-borono-L-phenylalanine

: 1849-02-1
2-chloro-1-methyl-benzimidazole

: 2-amino-3-[4-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-propionic acid

Conditions

Conditions	Yield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.0833333h; Suzuki coupling; Irradiation;	73%

: 24424-99-5
di-tert-butyl dicarbonate

: 76410-58-7
p-borono-L-phenylalanine

: 119771-23-2
N-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-1-phenylalanine

Conditions

Conditions	Yield
With sodium carbonate In water; acetone at 20℃; for 24h;	72%
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Product distribution / selectivity;
Stage #1: di-tert-butyl dicarbonate; p-borono-L-phenylalanine With potassium hydrogencarbonate In ethanol; water at 20℃; Stage #2: With potassium carbonate In ethanol; water at 20℃; for 2.5h;

: 76410-58-7
p-borono-L-phenylalanine

: 4659-45-4
2,6-Dichlorobenzoyl chloride

: 863228-94-8
(S)-2-(2,6-dichloro-benzoylamino)-3-(4-boronophenyl)-propionic acid

Conditions

Conditions	Yield
With sodium carbonate In water; acetonitrile at 50℃; for 1h;	71%
With sodium carbonate In water; acetonitrile
Stage #1: p-borono-L-phenylalanine; 2,6-Dichlorobenzoyl chloride With sodium carbonate In water; acetonitrile at 50℃; for 1h; Stage #2: With hydrogenchloride; water In acetonitrile at 0℃; for 0.5h; pH=2;
With sodium carbonate In acetonitrile

: 584-12-3
2-bromofuran

: 76410-58-7
p-borono-L-phenylalanine

: (S)-2-amino-3-(4-(furan-2-yl)phenyl)propanoic acid

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In acetonitrile at 150℃; for 0.5h; Suzuki Coupling; Microwave irradiation;	70%

: 214833-26-8
9-(2-deoxy-β-D-erythro-pentofuranosyl)-7-iodo-7-deazapurine 5'-O-triphosphate

: 76410-58-7
p-borono-L-phenylalanine

: (S)-2-amino-3-{4-[6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-7-deazapurin-7-yl]phenyl}propanoic acid 5'-O-triphosphate

Conditions

Conditions	Yield
With caesium carbonate; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 110℃; for 0.5h; Suzuki-Miyaura cross-coupling reaction;	66%

: 585-70-6
5-bromo-furan-2-carboxylic acid

: 76410-58-7
p-borono-L-phenylalanine

: (S)-5-(4-(2-amino-2-carboxyethyl)phenyl)furan-2-carboxylic acid

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In acetonitrile at 150℃; for 0.5h; Suzuki Coupling; Microwave irradiation;	64%

: 4594-45-0
6-chloropurine-2'-deoxyriboside

: 76410-58-7
p-borono-L-phenylalanine

: (S)-3-{4-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]phenyl}-2-aminopropanoic acid

Conditions

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; acetonitrile at 90℃; for 1.5h; Suzuki-Miyaura cross-coupling;	63%

: 945978-35-8
(5-bromo-pyrazin-2-yl)-(4'-methyl-biphenyl-2-ylmethyl)-amine

: 76410-58-7
p-borono-L-phenylalanine

: (S)-2-amino-3-(4-(5-((4'-methylbiphenyl-2-yl)methylamino)pyrazin-2-yl)phenyl)propanoic acid

Conditions

Conditions	Yield
Stage #1: (5-bromo-pyrazin-2-yl)-(4'-methyl-biphenyl-2-ylmethyl)-amine; p-borono-L-phenylalanine With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.0833333h; Suzuki Coupling; Microwave irradiation; Stage #2: Acidic conditions;	63%

: 945978-19-8
C18H18ClN5O

: 76410-58-7
p-borono-L-phenylalanine

: (S)-2-amino-3-(4-(4-morpholino-6-(naphthalen-2-ylmethylamino)-1,3,5-triazin-2-yl)phenyl)propanoic acid

Conditions

Conditions	Yield
Stage #1: C18H18ClN5O; p-borono-L-phenylalanine With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.0833333h; Suzuki Coupling; Microwave irradiation; Stage #2: With trifluoroacetic acid In methanol; water	63%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In acetonitrile at 150℃; for 0.166667h; Suzuki coupling; Microwave irradiation;

: 1928-76-3
9-benzyl-6-chloro-9H-purine

: 76410-58-7
p-borono-L-phenylalanine

: (S)-2-amino-3-[4-(9-benzylpurin-6-yl)phenyl]propionic acid hydrochloride

Conditions

Conditions	Yield
Stage #1: 9-benzyl-6-chloro-9H-purine; p-borono-L-phenylalanine With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 4h; Stage #2: With hydrogenchloride In 1,4-dioxane; water	61%

: 76410-58-7
p-borono-L-phenylalanine

: 159506-88-4
2-chloro-1-methyl-1H-indole-3-carbonitrile

: 2-amino-3-[4-(3-cyano-1-methyl-1H-indol-2-yl)-phenyl]-propionic acid

Conditions

Conditions	Yield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 150℃; for 0.166667h; Suzuki coupling; Irradiation;	60%

4-Borono-L-phenylalanine Specification

The L-Phenylalanine,4-borono-, with the CAS registry number 76410-58-7, has the systematic name and IUPAC name of 4-(dihydroxyboranyl)-L-phenylalanine. It is a kind of white to off-white powder, and belongs to the product category of Boronic Acids. And the molecular formula of the chemical is C₉H₁₂BNO₄. What's more, it should be stored at 2-8°C. Neutron absorbing (10)B-cpd used in thermal neutron capturetherapy of malignant melanoma. It is a white to off-white powder.

The characteristics of 4-Borono-L-phenylalanine are as followings:
(1)ACD/LogP: 0.49; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -2.01; (4)ACD/LogD (pH 7.4): -2.05; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 48 Å²; (13)Index of Refraction: 1.59; (14)Molar Refractivity: 52.42 cm³; (15)Molar Volume: 155.1 cm³; (16)Polarizability: 20.78×10^-24cm³; (17)Surface Tension: 64.6 dyne/cm; (18)Density: 1.34 g/cm³; (19)Flash Point: 225.5 °C; (20)Enthalpy of Vaporization: 74.61 kJ/mol; (21)Boiling Point: 449.3 °C at 760 mmHg; (22)Vapour Pressure: 7.39E-09 mmHg at 25°C.

Safety Information of 4-Borono-L-phenylalanine :
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(O)[C@@H](N)Cc1ccc(cc1)B(O)O
(2)InChI: InChI=1/C9H12BNO4/c11-8(9(12)13)5-6-1-3-7(4-2-6)10(14)15/h1-4,8,14-15H,5,11H2,(H,12,13)/t8-/m0/s1
(3)InChIKey: NFIVJOSXJDORSP-QMMMGPOBBD

Product Name

4-BORONO-L-PHENYLALANINE

Synthetic route

4-Borono-L-phenylalanine Specification

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