Boc-O-benzyl-L-tyrosine supplier

Name
Boc-O-benzyl-L-tyrosine
EINECS 218-349-4
CAS No. 2130-96-3
Article Data26
CAS DataBase
Density 1.185 g/cm³
Solubility Insoluble in water and petroleum ether
Melting Point 110-112 °C
Formula C₂₁H₂₅NO₅
Boiling Point 552.4 °C at 760 mmHg
Molecular Weight 371.433
Flash Point 287.9 °C
Transport Information
Appearance White crystalline powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms O-Benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine;(2S)-3-(4-phenylmethoxyphenyl)-2-(tert-butoxycarbonylamino)propanoate;3-(4-phenylmethoxyphenyl)-2-(tert-butoxycarbonylamino)propanoic acid;BOC-L-Tyr(Bzl)-OH;O-benzyl-N-[(tert-butoxy)carbonyl]-L-tyrosine;
PSA 84.86000
LogP 4.17690

Synthetic route

: 3978-80-1
Boc-Tyr-OH

: 100-39-0
benzyl bromide

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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;

: 3978-80-1
Boc-Tyr-OH

: 100-44-7
benzyl chloride

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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%

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

: 100-39-0
benzyl bromide

: 60-18-4
L-tyrosine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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%

...Expand

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

: 16652-64-5
O-benzyl-S-tyrosine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

: 3978-80-1
Boc-Tyr-OH

benzyl halide: benzyl halide

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

: 16652-64-5
O-benzyl-S-tyrosine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

: 1070-19-5
N-(tert-butyloxycarbonyl) azide

: 16652-64-5
O-benzyl-S-tyrosine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 16965-08-5
1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate

: 16652-64-5
O-benzyl-S-tyrosine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

Conditions	Yield
With triethylamine In tert-butyl alcohol

: 16652-64-5
O-benzyl-S-tyrosine

: 24608-52-4
tert-butyl chloroformate

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

Conditions	Yield
With sodium hydroxide

: 1070-19-5
N-(tert-butyloxycarbonyl) azide

: 2130-95-2
O'-benzyl-L-tyrosine ethyl ester hydrochloride

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

: 100-39-0
benzyl bromide

XOOC-CH2-COOX: XOOC-CH2-COOX

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

: 60-18-4
L-tyrosine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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: (Boc)2 O

: 16652-64-5
O-benzyl-S-tyrosine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

: 27513-44-6
N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

: 100-44-7
benzyl chloride

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 60-18-4
L-tyrosine

Conditions

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%

: 67-56-1
methanol

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 57177-83-0
O-benzyltyrosine methyl ester

Conditions

Conditions	Yield
With thionyl chloride for 18h;	100%

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 1562429-74-6
(S)-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

: 1562429-75-7
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

Conditions

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%

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%

: 67-56-1
methanol

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 34805-17-9
methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 74-88-4
methyl iodide

: 64263-81-6
N-(tert-butyloxycarbonyl)-N-methyl-O-(phenylmethyl)-L-tyrosine

Conditions

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%

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 126410-45-5
tert-butyl (S)-{3-[4-(benzyloxy)phenyl]-1-[methoxy(methyl)amino]-1-oxo-propan-2-yl}carbamate

Conditions

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;

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 66605-58-1
O-benzyl N-Boc-L-tyrosinol

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 91837-50-2
N-trichloroacetoxyphthalimide

: (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: Leu-Trp-OMe trifluoroacetate

: Boc-Thr(Bn)-Leu-Trp-OMe

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 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

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%

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 589-08-2
N-Methyl-N-phenethylamine

: 173899-80-4
N-[Boc-(O-benzyl)-L-tyrosyl]-N-methyl-2-phenylethylamine

Conditions

Conditions	Yield
	97%

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 4381-25-3, 33903-50-3, 60933-65-5, 81162-81-4
(S)-S-methyl-S-phenylsulfoximine

: N-[Boc-L-Tyr(Bn)]-(S)-S-methyl-S-phenylsulfoximine

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 655250-09-2
N8-(4-amino-1-methylpentyl)-2-tert-butyl-6-methoxy-8-quinolinamine

: 925934-42-5
(S)-(2-(4-benzyloxyphenyl)-1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]ethyl)carbamic acid tert-butyl ester

Conditions

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

: 629-41-4
1,8-Octanediol

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: bis-N-Boc-O-benzl-L-tyrosine-octane-1,8-diester

Conditions

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

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 54613-99-9
Boc-(S)-Lys(2-Cl-Z)-OH

: 78981-22-3
3-<(4-methylbenzyl)thio>propionic acid

Boc-Gly-Merrifield resinBoc-Arg(Tos): Boc-Gly-Merrifield resinBoc-Arg(Tos)

: C84H101ClN14O15S3

Conditions

Conditions	Yield
Multistep reaction;	96.6%

...Expand

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 2133-40-6
L-proline methyl ester monohydrochloride

: 140685-07-0
N-t-butoxycarbonyl-(S)-O-benzyltyrosyl-(S)-proline methyl ester

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: Thr(Bzl)-Pro-Lys(Pipoc)-Ala-OPic

: 76369-80-7
Boc-Tyr(Bzl)-Thr(Bzl)-Pro-Lys(Pipoc)-Ala-OPic

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 35229-21-1
Boc-Tyr(Bzl)-NH2

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: (2R)-2-Benzyl-3-oxopyrrolidininium trifluoroacetate

: (2R)-2-Benzyl-1-O-benzyl-[N-(tert-butoxycarbonyl)-L-tyrosinyl]pyrrolidin-3-one

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: (2S)-2-Benzyl-3-oxopyrrolidininium trifluoroacetate

: (2S)-2-Benzyl-1-O-benzyl-[N-(tert-butoxycarbonyl)-L-tyrosinyl]pyrrolidin-3-one

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: (2R,3R)-2-Benzyl-3-(benzyloxy)pyrrolidininium trifluoroacetate

: (2R,3R)-2-Benzyl-1-O-benzyl-1-[N-(tert-butoxycarbonyl)-L-tyrosinyl]-3-benzyloxypyrrolidine

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 34805-17-9
methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride

: t-Boc-L-tyrosyl(O-benzyl)-L-tyrosine(O-benzyl)methyl ester

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 613-94-5
benzoic acid hydrazide

: 888019-70-3
[2-(N'-benzoyl-hydrazino)-1-(4-benzyloxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Conditions

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%

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: (2S,3S)-2-Benzyl-3-(benzyloxy)pyrrolidininium trifluoroacetate

: (2S,3S)-2-Benzyl-1-O-benzyl-1-[N-(tert-butoxycarbonyl)-L-tyrosinyl]-3-benzyloxypyrrolidine

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 175214-21-8
Tyr(MPM)-OMe

: 187328-92-3
Boc-Tyr(Bn)-Tyr(MPM)-OMe

Conditions

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

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 127946-77-4
1-amino-1-cyclopropanecarbonitrile hydrochloride

: C25H29N3O4

Conditions

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%

: 15761-39-4
1-(tert-butoxycarbonyl)-L-proline

: 13139-15-6
N-tert-butoxycarbonyl-L-leucine

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 78981-22-3
3-<(4-methylbenzyl)thio>propionic acid

Boc-Gly-Merrifield resinBoc-Orn(Z): Boc-Gly-Merrifield resinBoc-Orn(Z)

: C77H95N11O14S2

Conditions

Conditions	Yield
Multistep reaction;	94.7%

...Expand

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 623-33-6
glycine ethyl ester hydrochloride

: 40356-35-2
BOC-Tyr(OBzl)-Gly-OEt

Conditions

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%

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

: 2087-41-4
glycyl glycine ethyl ester hydrochloride

: 87423-40-3
Boc-Tyr(OBzl)-Gly-Gly-OEt

Conditions

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%

Boc-O-benzyl-L-tyrosine Specification

The IUPAC name of Boc-O-benzyl-L-tyrosine is 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylmethoxyphenyl) propanoic acid . With the CAS registry number 2130-96-3, it is also named as O-Benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine ; L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- ; N-(tert-Butoxycarbonyl)-O-benzyl-L-tyrosine .

The product's categories are Protected Amino Acids, Amino Acids, Tyrosine [Tyr, Y], Boc-Amino Acids and Derivative, Biochemistry and Boc-Amino acid series. Boc-O-benzyl-L-tyrosine is white crystalline powder which is insoluble in water and petroleum ether , dissolved in ethyl acetate and ethanol . It is used to protect amino acids in peptide synthesis. People should not breathe the dust of this product and must avoid contact with skin and eyes.

The Boc-O-benzyl-L-tyrosine can be obtained by the following method. The O-benzyl-L-tyrosine suspends in dioxane solution, and then the crude product is obtained by the acylation reaction with tert-Butoxycarbonyl azide . At pH 9-10, using ethyl acetate to extract, then we can get the product by recrystallization purification.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.53 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 2.52 ; (4)ACD/LogD (pH 7.4): 1.01 ; (5)ACD/BCF (pH 5.5): 15.74 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 66.78 ; (8)ACD/KOC (pH 7.4): 2.07 ; (9)#H bond acceptors: 6 ; (10)#H bond donors: 2 ; (11)#Freely Rotating Bonds: 9 ; (12)Index of Refraction: 1.562 ; (13)Molar Refractivity: 101.62 cm³ ; (14)Molar Volume: 313.3 cm³ ; (15)Polarizability: 40.28×10^-24 cm³ ; (16)Surface Tension: 46.5 dyne/cm ; (17)Enthalpy of Vaporization: 87.66 kJ/mol ; (18)Vapour Pressure: 4.87E-13 mmHg at 25°C ; (19)Rotatable Bond Count: 9 ; (20)Tautomer Count: 2 ; (21)Exact Mass: 371.173273 ; (22)MonoIsotopic Mass: 371.173273 ; (23)Topological Polar Surface Area: 84.9 ; (24)Heavy Atom Count: 27.

People can use the following data to convert to the molecule structure. SMILES: O=C(OC(C)(C)C)N[C@H](C(=O)O)Cc2ccc(OCc1ccccc1)cc2; 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)/t18-/m0/s1.

Product Name

Boc-O-benzyl-L-tyrosine

Synthetic route

Boc-O-benzyl-L-tyrosine Specification

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