2130-96-3

Basic information

• Product Name: Boc-O-benzyl-L-tyrosine
• Synonyms: T-BUTYLOXYCARBONYL-O-BENZYL-L-TYROSINE;N-BOC-O-BENZYL-L-TYROSINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-O-BENZYL-L-TYROSINE;N-ALPHA-T-BUTOXYCARBONYL-O-BENZYL-L-TYROSINE;N-ALPHA-T-BOC-O-BENZYL-L-TYROSINE;N-(TERT-BUTOXYCARBONYL)-O-BENZYL-L-TYROSINE;N-TERT-BUTOXYCARBONYL-O-BENZYL-L-TYRISINE;N-T-BUTOXYCARBONYL-O-BENZYL-L-TYROSINE
• CAS NO: 2130-96-3
• Molecular Formula: C₂₁H₂₅NO₅
• Molecular Weight: 371.43
• EINECS: 218-349-4
• Product Categories: Protected Amino Acids;Amino Acids;Tyrosine [Tyr, Y];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 2130-96-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 110-112 °C
• Boiling Point: 552.4 °C at 760 mmHg
• Flash Point: 287.9 °C
• Appearance: White/Powder or Crystalline Powder
• Density: 1.185 g/cm³
• Vapor Pressure: 4.87E-13mmHg at 25°C
• Refractive Index: 29.5 ° (C=2, EtOH)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in EtOH
• PKA: 2.99±0.10(Predicted)
• BRN: 2227416
• CAS DataBase Reference: Boc-O-benzyl-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-O-benzyl-L-tyrosine(2130-96-3)
• EPA Substance Registry System: Boc-O-benzyl-L-tyrosine(2130-96-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2130-96-3(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Uses

Boc-Tyr(Bzl)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

InChI:InChI=1/C21H25NO5/c1-21(2,3)27-20(25)22-18(19(23)24)13-15-9-11-17(12-10-15)26-14-16-7-5-4-6-8-16/h4-12,18H,13-14H2,1-3H3,(H,22,25)(H,23,24)/p-1/t18-/m0/s1

Synthetic route

Boc-Tyr-OH (3978-80-1) + benzyl bromide (100-39-0) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With sodium methylate; tetra-(n-butyl)ammonium iodide In methanol at 40℃; for 3h;	95%
Stage #1: Boc-Tyr-OH With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	91%
With sodium methylate In methanol at 40℃; for 3h;	64%
Stage #1: Boc-Tyr-OH; benzyl bromide With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h; Stage #2: With sodium hydroxide In 1,4-dioxane at 20℃; for 24h;

Boc-Tyr-OH (3978-80-1) + benzyl chloride (100-44-7) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
Stage #1: Boc-Tyr-OH; benzyl chloride With sodium methylate; tetra-(n-butyl)ammonium iodide In methanol at 40℃; for 24h; Stage #2: With hydrogenchloride In methanol; water	84%

di-tert-butyl dicarbonate (24424-99-5) + benzyl bromide (100-39-0) + L-tyrosine (60-18-4) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
Stage #1: L-tyrosine With sodium hydroxide In water for 1.5h; Stage #2: copper(II) sulfate In water for 0.5h; Stage #3: di-tert-butyl dicarbonate; benzyl bromide	80%
Stage #1: L-tyrosine With copper(ll) sulfate pentahydrate; sodium hydroxide In water at 60℃; for 1.5h; Stage #2: benzyl bromide In methanol; water at 60℃; for 3h; Stage #3: di-tert-butyl dicarbonate Further stages;	46%
Stage #1: L-tyrosine With copper(II) sulfate; sodium hydroxide at 60℃; for 1h; Stage #2: benzyl bromide In methanol at 60℃; for 3h; Stage #3: di-tert-butyl dicarbonate With triethylamine In 1,4-dioxane; water at 0 - 20℃;	46%

di-tert-butyl dicarbonate (24424-99-5) + O-benzyl-S-tyrosine (16652-64-5) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 20 - 40℃; for 18h; pH=10.4;	70%
In water; tert-butyl alcohol pH 9.5-10.0;
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane at 20℃;
With sodium hydroxide In water; tert-butyl alcohol at 20℃;	2.46 g
Stage #1: O-benzyl-S-tyrosine With sodium hydroxide In water; tert-butyl alcohol Cooling with ice; Stage #2: di-tert-butyl dicarbonate In water; tert-butyl alcohol at 20℃; Stage #3: With hydrogenchloride In water; tert-butyl alcohol	2.46 g

Boc-Tyr-OH (3978-80-1) + benzyl halide → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	34%

O-benzyl-S-tyrosine (16652-64-5) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With 1,4-dioxane; sodium hydroxide anschliessendes Erwaermen mit Azidokohlensaeure-tert-butylester;

N-(tert-butyloxycarbonyl) azide (1070-19-5) + O-benzyl-S-tyrosine (16652-64-5) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate (16965-08-5) + O-benzyl-S-tyrosine (16652-64-5) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With triethylamine In tert-butyl alcohol

O-benzyl-S-tyrosine (16652-64-5) + tert-butyl chloroformate (24608-52-4) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With sodium hydroxide

N-(tert-butyloxycarbonyl) azide (1070-19-5) + O'-benzyl-L-tyrosine ethyl ester hydrochloride (2130-95-2) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
(i) aq. K2CO3, (ii) /BRN= 1363586/, Py, (iii) aq. NaOH; Multistep reaction;

benzyl bromide (100-39-0) + XOOC-CH2-COOX → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aq. NaOH; CuSO4*5H2O / 1 h / Heating 1.2: 73 percent / aq. NaOH / methanol / 20 °C 2.1: aq. NaOH; NaHCO3 / dioxane / 20 °C View Scheme

L-tyrosine (60-18-4) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aq. NaOH; CuSO4*5H2O / 1 h / Heating 1.2: 73 percent / aq. NaOH / methanol / 20 °C 2.1: aq. NaOH; NaHCO3 / dioxane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / water; tetrahydrofuran / 20 °C 2: sodium methylate / methanol / 3 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: water; 1,4-dioxane / 18 h / 20 °C / Cooling with ice 2.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 48 h / 20 °C 2.2: 24 h / 20 °C View Scheme

(Boc)2 O + O-benzyl-S-tyrosine (16652-64-5) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With triethylamine; citric acid In 1,4-dioxane; water

di-tert-butyl dicarbonate (24424-99-5) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; tetrahydrofuran / 20 °C 2: sodium methylate / methanol / 3 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: water; 1,4-dioxane / 18 h / 20 °C / Cooling with ice 2.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 48 h / 20 °C 2.2: 24 h / 20 °C View Scheme

N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester (27513-44-6) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetone / 70 °C 2: sodium hydroxide / methanol; dichloromethane View Scheme

benzyl chloride (100-44-7) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetone / 70 °C 2: sodium hydroxide / methanol; dichloromethane View Scheme

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) → L-tyrosine (60-18-4)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h;	100%
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;	100%
With dimethylsulfide; hydrogen fluoride at 0℃; for 2h; Product distribution; Var.: HF in anisole;	99.5%

methanol (67-56-1) + O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) → O-benzyltyrosine methyl ester (57177-83-0)

Conditions	Yield
With thionyl chloride for 18h;	100%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + (S)-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide (1562429-74-6) → tert-butyl ((S)-3-(4-(benzyloxy)phenyl)-1-oxo-1-((S)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-yl)carbamate (1562429-75-7)

Conditions

Yield

Stage #1: O-benzyl-N-tert-butoxycarbonyl-L-tyrosine With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: (S)-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide With 4-methyl-morpholine In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;

100%

methanol (67-56-1) + O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) → methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride (34805-17-9)

Conditions	Yield
With thionyl chloride for 3h; Heating;	100%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + methyl iodide (74-88-4) → N-(tert-butyloxycarbonyl)-N-methyl-O-(phenylmethyl)-L-tyrosine (64263-81-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran; paraffin a) 0 deg C, 1 h, b) 25 deg C, 16 h;	99%
Stage #1: O-benzyl-N-tert-butoxycarbonyl-L-tyrosine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 24h;	98%
With sodium hydride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Cooling with ice;	98%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → tert-butyl (S)-{3-[4-(benzyloxy)phenyl]-1-[methoxy(methyl)amino]-1-oxo-propan-2-yl}carbamate (126410-45-5)

Conditions	Yield
Stage #1: O-benzyl-N-tert-butoxycarbonyl-L-tyrosine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 25℃; for 14h; Inert atmosphere;	99%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	90%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane	87%
With TEA; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 0℃; Acylation;

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) → O-benzyl N-Boc-L-tyrosinol (66605-58-1)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 20℃; for 4.33333h; Inert atmosphere;	99%
With diborane at -10 - 25℃; for 6h; Inert atmosphere;	80%
Stage #1: O-benzyl-N-tert-butoxycarbonyl-L-tyrosine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -10℃; Stage #2: With sodium tetrahydroborate In tetrahydrofuran

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + N-trichloroacetoxyphthalimide (91837-50-2) → (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

Conditions	Yield
With pyridine In acetonitrile at 22 - 23℃; for 12h; further solvents;	98%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + Leu-Trp-OMe trifluoroacetate → Boc-Thr(Bn)-Leu-Trp-OMe

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran	98%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + 2-methyl-1-[1,2,4]triazolo[3,4-a]phthalazin-3-yl-propylamine p-toluenesulphonate salt → [2-(4-benzyloxy-phenyl)-1-(2-methyl-1-[1,2,4]triazolo[3,4-a]phthalazin-3-yl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃;	97.65%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + N-Methyl-N-phenethylamine (589-08-2) → N-[Boc-(O-benzyl)-L-tyrosyl]-N-methyl-2-phenylethylamine (173899-80-4)

Conditions	Yield
	97%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + (S)-S-methyl-S-phenylsulfoximine (4381-25-3, 33903-50-3, 60933-65-5, 81162-81-4) → N-[Boc-L-Tyr(Bn)]-(S)-S-methyl-S-phenylsulfoximine

Conditions	Yield
With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 13h;	97%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + N8-(4-amino-1-methylpentyl)-2-tert-butyl-6-methoxy-8-quinolinamine (655250-09-2) → (S)-(2-(4-benzyloxyphenyl)-1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]ethyl)carbamic acid tert-butyl ester (925934-42-5)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	97%

1,8-Octanediol (629-41-4) + O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) → bis-N-Boc-O-benzl-L-tyrosine-octane-1,8-diester

Conditions	Yield
With 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide In dichloromethane at 0℃; Inert atmosphere;	97%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + Boc-(S)-Lys(2-Cl-Z)-OH (54613-99-9) + 3-<(4-methylbenzyl)thio>propionic acid (78981-22-3) + Boc-Gly-Merrifield resinBoc-Arg(Tos) → C84H101ClN14O15S3

Conditions	Yield
Multistep reaction;	96.6%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + L-proline methyl ester monohydrochloride (2133-40-6) → N-t-butoxycarbonyl-(S)-O-benzyltyrosyl-(S)-proline methyl ester (140685-07-0)

Conditions	Yield
With triethylamine; dicyclohexyl-carbodiimide In chloroform at 0℃;	96%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + Thr(Bzl)-Pro-Lys(Pipoc)-Ala-OPic → Boc-Tyr(Bzl)-Thr(Bzl)-Pro-Lys(Pipoc)-Ala-OPic (76369-80-7)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran	96%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) → Boc-Tyr(Bzl)-NH2 (35229-21-1)

Conditions	Yield
With ammonium bicarbonate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In chloroform Ambient temperature;	96%
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate In 1,4-dioxane 4-16 h;	76%
Stage #1: O-benzyl-N-tert-butoxycarbonyl-L-tyrosine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.25h; Stage #2: With ammonium hydroxide In tetrahydrofuran

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + (2R)-2-Benzyl-3-oxopyrrolidininium trifluoroacetate → (2R)-2-Benzyl-1-O-benzyl-[N-(tert-butoxycarbonyl)-L-tyrosinyl]pyrrolidin-3-one

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃;	96%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + (2S)-2-Benzyl-3-oxopyrrolidininium trifluoroacetate → (2S)-2-Benzyl-1-O-benzyl-[N-(tert-butoxycarbonyl)-L-tyrosinyl]pyrrolidin-3-one

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 2h;	96%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + (2R,3R)-2-Benzyl-3-(benzyloxy)pyrrolidininium trifluoroacetate → (2R,3R)-2-Benzyl-1-O-benzyl-1-[N-(tert-butoxycarbonyl)-L-tyrosinyl]-3-benzyloxypyrrolidine

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃;	96%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride (34805-17-9) → t-Boc-L-tyrosyl(O-benzyl)-L-tyrosine(O-benzyl)methyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran	96%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + benzoic acid hydrazide (613-94-5) → [2-(N'-benzoyl-hydrazino)-1-(4-benzyloxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (888019-70-3)

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	96%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + (2S,3S)-2-Benzyl-3-(benzyloxy)pyrrolidininium trifluoroacetate → (2S,3S)-2-Benzyl-1-O-benzyl-1-[N-(tert-butoxycarbonyl)-L-tyrosinyl]-3-benzyloxypyrrolidine

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 3h;	95%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + Tyr(MPM)-OMe (175214-21-8) → Boc-Tyr(Bn)-Tyr(MPM)-OMe (187328-92-3)

Conditions	Yield
With diphenylphosphoranyl azide In N,N-dimethyl-formamide at 20℃; for 12h;	95%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + 1-amino-1-cyclopropanecarbonitrile hydrochloride (127946-77-4) → C25H29N3O4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 22℃; Inert atmosphere;	95%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4) + N-tert-butoxycarbonyl-L-leucine (13139-15-6) + O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + 3-<(4-methylbenzyl)thio>propionic acid (78981-22-3) + Boc-Gly-Merrifield resinBoc-Orn(Z) → C77H95N11O14S2

Conditions	Yield
Multistep reaction;	94.7%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + glycine ethyl ester hydrochloride (623-33-6) → BOC-Tyr(OBzl)-Gly-OEt (40356-35-2)

Conditions	Yield
With O-Benzotriazol-1-yl-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.25h; Ambient temperature;	94.5%
With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h; Ambient temperature;	94%
With N-ethylmorpholine;; benzotriazol-1-ol; dicyclohexyl-carbodiimide In 1,4-dioxane 1.) -10 deg C, 0.5 h, 2.) room temperature, 16 h;	93%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + glycyl glycine ethyl ester hydrochloride (2087-41-4) → Boc-Tyr(OBzl)-Gly-Gly-OEt (87423-40-3)

Conditions	Yield
With N-ethylmorpholine;; benzotriazol-1-ol; dicyclohexyl-carbodiimide In 1,4-dioxane 1.) -10 deg C, 0.5 h, 2.) room temperature, 16 h;	94%

Upstream product

• 3978-80-1 Boc-Tyr-OH 
• 100-44-7 benzyl chloride 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 27513-44-6 N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-39-0 benzyl bromide 
• 60-18-4 L-tyrosine 
• 16652-64-5 O-benzyl-S-tyrosine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2130-95-2 O'-benzyl-L-tyrosine ethyl ester hydrochloride 
• 24608-52-4 tert-butyl chloroformate 
• 16965-08-5 1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate 

Downstream Products

• 76370-02-0 N-t-butoxycarbonyl-O-benzyl-L-tyrosine 4-picolyl ester 
• 74814-07-6 Tyr-D-Ala-Gly-Phe(αMe) 
• 74814-06-5 Tyr-D-Ala-Gly-Phe(αMe)-Leu 
• 65638-82-6 N-Boc-Tyr(Bzl)-Leu-OMe 
• 77935-34-3 Boc-Tyr(Bzl)-His-OMe 
• 27513-44-6 N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester 
• 216392-34-6 1-[(tert-butoxycarbonyl)-L-(O-benzyl)tyrosyl]-3(R,S)-pyrrolidinol 
• 92515-43-0 (S)-3-(4-benzyloxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid benzyl ester 
• 173899-80-4 N-[Boc-(O-benzyl)-L-tyrosyl]-N-methyl-2-phenylethylamine 
• 61884-33-1 Boc-Tyr(Bzl)-Pro-OBzl 
• 187328-92-3 Boc-Tyr(Bn)-Tyr(MPM)-OMe 
• 777952-60-0 N-[N-(tert-butyloxycarbonyl)-O-(benzyl)-tyrosyl]-octadecylamine 
• 17693-22-0 N-t-Butyloxycarbonyl-O-benzyl-L-tyrosin-pentachlorphenylester 
• 16652-64-5 O-benzyl-S-tyrosine 

Relevant articles and documents

Discovery and development of substituted tyrosine derivatives as Bcl-2/Mcl-1 inhibitors

Anti-apoptotic Bcl-2 family proteins are vital for cancer cells to escape apoptosis, which make them attractive targets for cancer therapy. Recently, a lead compound 1 was found to modestly inhibit the binding of BH3 peptide to Bcl-2 protein with a Ki value of 5.2 μM. Based on this, a series of substituted tyrosine derivatives were developed and tested for their binding affinities to Bcl-2 protein. Results indicated that these compounds exhibited potent binding affinities to Bcl-2 and Mcl-1 protein but not to Bcl-XL protein. Promisingly, compound 6i inhibited the binding of BH3 peptide to Bcl-2 and Mcl-1 protein with a Ki value of 450 and 190 nM respectively, and showed obvious anti-proliferative activities against tested cancer cells.

Design, synthesis and preliminary bioactivity studies of indomethacin derivatives as Bcl-2/Mcl-1 dual inhibitors

Bcl-2 family proteins, which divides into pro-apoptosis proteins and anti-apoptosis proteins, are involved in cell apoptosis progression. As numerous studies illustrated, targeting Bcl-2 family proteins is more and more attractive and practicable to cancer treatment. In this work, we designed and synthesized a series of indomethacin derivatives as new inhibitors for Bcl-2 family proteins. Our results of binding assay to Bcl-2 proteins, MTT assay and apoptotic assay indicated that some compounds had potent binding affinity to Bcl-2/Mcl-1 but not Bcl-XL. Furthermore, compound 8j showed improved anti-proliferative activity than known Bcl-2 inhibitor WL-276.

Improved binding affinities of pyrrolidine derivatives as Mcl-1 inhibitors by modifying amino acid side chains

As an important member of anti-apoptotic Bcl-2 protein, myeloid cell leukemia sequence 1 (Mcl-1) protein is an attractive target for cancer therapy. In this study, a new series of pyrrolidine derivatives as Mcl-1 inhibitors were developed by mainly modifying the amino acid side chain of compound 1. Among them, compound 18 (Ki= 0.077 μM) exhibited better potent inhibitory activities towards Mcl-1 protein compared to positive control Gossypol (Ki= 0.18 μM). In addition, compound 40 possessed good antiproliferative activities against PC-3 cells (Ki= 8.45 μM), which was the same as positive control Gossypol (Ki= 7.54 μM).