Product Name

  • Name

    H-TYR(BZL)-OH

  • EINECS 240-699-1
  • CAS No. 16652-64-5
  • Article Data18
  • CAS DataBase
  • Density 1.221 g/cm3
  • Solubility
  • Hazard Symbols Not regulated UN NO.
  • Synonyms Alanine,3-[p-(benzyloxy)phenyl]-, L- (8CI); NSC 163630; O-Benzyl-L-tyrosine;O-Benzyltyrosine; Tyrosine benzyl ether
  • PSA 72.55000
  • LogP 2.92030

Synthetic route

O-benzyl-L-tyrosine coper complex

O-benzyl-L-tyrosine coper complex

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
With sodium sulfide In water at 25 - 30℃; for 0.166667h;93%
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine
2130-96-3

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
With ammonia; hydrogen; palladium on activated charcoal In methanol for 0.5h; Ambient temperature;89%
With hydrogenchloride In diethyl ether Hydrolysis;
With trifluoroacetic acid at 20℃; for 0.25h;
Oϖ-Bzl-L-Tur/copper complex

Oϖ-Bzl-L-Tur/copper complex

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
With N,N-Dibutyl-N'-(benzoyl)thioharnstoff In ethanol for 2h; Heating;80%
benzyl bromide
100-39-0

benzyl bromide

L-tyrosine
60-18-4

L-tyrosine

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
Stage #1: L-tyrosine With sodium hydroxide; copper(II) sulfate for 1h; Heating;
Stage #2: benzyl bromide With sodium hydroxide In methanol at 20℃;		73%
Stage #1: L-tyrosine With copper(ll) sulfate pentahydrate; sodium hydroxide In water at 70℃; for 1h;
Stage #2: benzyl bromide With sodium hydroxide In methanol at 70℃; for 0.5h;		68%
Stage #1: L-tyrosine With copper(ll) sulfate pentahydrate; sodium hydroxide In water at 20 - 70℃;
Stage #2: benzyl bromide With sodium hydroxide In methanol; water Enzymatic reaction;
Stage #3: With edetate disodium In water at 70℃; for 4.5h;		68%
L-tyrosine
60-18-4

L-tyrosine

benzyl chloride
100-44-7

benzyl chloride

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
Stage #1: L-tyrosine With potassium hydroxide; copper(II) sulfate In water at 15 - 65℃; for 1h;
Stage #2: benzyl chloride In water; N,N-dimethyl-formamide at 20 - 55℃; for 2h;
Stage #3: With hydrogenchloride; ammonia more than 3 stages;		62%
O-benzyl-L-tyrosine coper complex

O-benzyl-L-tyrosine coper complex

hydrogenchloride
7647-01-0

hydrogenchloride

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
Stage #1: O-benzyl-L-tyrosine coper complex; hydrogenchloride In water at 26 - 28℃;
Stage #2: With ammonia In water Product distribution / selectivity;		46%
benzyl bromide
100-39-0

benzyl bromide

copper (II)-salt of L-tyrosine

copper (II)-salt of L-tyrosine

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
With sodium hydroxide
With sodium hydroxide
copper(I) sulfate

copper(I) sulfate

L-tyrosine
60-18-4

L-tyrosine

benzyl chloride
100-44-7

benzyl chloride

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
With copper(II) sulfate In methanol; sodium hydroxide; water
...Expand
copper(I) sulfate

copper(I) sulfate

benzyl bromide
100-39-0

benzyl bromide

L-tyrosine
60-18-4

L-tyrosine

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

O-benzyl-S-tyrosine

Conditions
ConditionsYield
With copper(II) sulfate In methanol; sodium hydroxide; water
With copper(II) sulfate In methanol; sodium hydroxide; water
With copper(II) sulfate In methanol; sodium hydroxide; water
...Expand
ethanol
64-17-5

ethanol

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

O-benzyl-S-tyrosine

O-benzyl L-tyrosine ethyl ester
19842-36-5

O-benzyl L-tyrosine ethyl ester

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 12h;100%
With hydrogenchloride
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

Heptanoic acid chloride
2528-61-2

Heptanoic acid chloride

(S)-3-(4-Benzyloxy-phenyl)-2-heptanoylamino-propionic acid
196704-18-4

(S)-3-(4-Benzyloxy-phenyl)-2-heptanoylamino-propionic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran for 4h; Ambient temperature;99%
With sodium hydroxide In tetrahydrofuran; water for 5h; Acylation;99%
Ala-OtBu
21691-50-9

Ala-OtBu

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

O-benzyl-S-tyrosine

H-L-Tyr(Bn)-L-Ala-OtBu

H-L-Tyr(Bn)-L-Ala-OtBu

Conditions
ConditionsYield
Stage #1: O-benzyl-S-tyrosine With 1H-imidazole; tris[(1,1,1,3,3,3-hexafluoropropan-2-yl)oxy]silane; cesium fluoride In chloroform at 30℃; for 1h; Inert atmosphere; Sealed tube;
Stage #2: With N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide In chloroform at 30℃; for 1h; Inert atmosphere; Sealed tube;
Stage #3: Ala-OtBu In chloroform at 30℃; for 6h; Inert atmosphere; Sealed tube;		99%
methanol
67-56-1

methanol

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

O-benzyl-S-tyrosine

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

methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride

Conditions
ConditionsYield
With thionyl chloride for 72h; Ambient temperature;98%
With thionyl chloride at 0℃; Reflux;90%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

benzyl chloroformate
501-53-1

benzyl chloroformate

N-benzyloxycarbonyl-O-benzyl-L-tyrosine
86827-18-1, 92455-53-3, 16677-29-5

N-benzyloxycarbonyl-O-benzyl-L-tyrosine

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 2h;95%
With sodium hydroxide
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

N-Carboxy-O-benzyl-L-tyrosine Anhydride
22831-96-5

N-Carboxy-O-benzyl-L-tyrosine Anhydride

Conditions
ConditionsYield
In tetrahydrofuran at 55℃; for 2h; Temperature;93.3%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

2-[4-(benzyloxy)phenyl]acetonitrile
838-96-0

2-[4-(benzyloxy)phenyl]acetonitrile

Conditions
ConditionsYield
With sodium hydroxide; trichloroisocyanuric acid at 25℃; for 1h;93%
pentamethylbenzene,
700-12-9

pentamethylbenzene,

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

O-benzyl-S-tyrosine

(2,3,4,5,6-pentamethylphenyl)phenylmethane
39502-94-8

(2,3,4,5,6-pentamethylphenyl)phenylmethane

Conditions
ConditionsYield
With trifluoroacetic acid for 7h; Ambient temperature;91%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

cobalt(II) chloride
7646-79-9

cobalt(II) chloride

[(C6H5CH2OC6H4CH2CH(NH2)COO)2Co]

[(C6H5CH2OC6H4CH2CH(NH2)COO)2Co]

Conditions
ConditionsYield
In tetrahydrofuran mixing of soln. of PhCH2OC6H4CH2CH(NH2)CO2H in THF with CoCl2 (0.5 equiv.), stirring for 3 h at 50-60°C; removal of solvent, washing several times with Et2O, MeOH and H2O, elem.anal.;90%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

(Z)-3-[(S)-2-(4-Benzyloxy-phenyl)-1-carboxy-ethylamino]-but-2-enoic acid ethyl ester; compound with dicyclohexyl-amine
114671-46-4

(Z)-3-[(S)-2-(4-Benzyloxy-phenyl)-1-carboxy-ethylamino]-but-2-enoic acid ethyl ester; compound with dicyclohexyl-amine

Conditions
ConditionsYield
In methanol; ethanol; water for 3h; Heating;89%
...Expand
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

2,2,2-Trichloroethyl chloroformate
17341-93-4

2,2,2-Trichloroethyl chloroformate

O-benzyl-N-Tcc-L-tyrosine
37888-25-8

O-benzyl-N-Tcc-L-tyrosine

Conditions
ConditionsYield
In ethyl acetate Heating;85%
2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate
3496-11-5

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

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

O-benzyl-S-tyrosine

N-benzoxycarbonyl-L-valyl-O-benzyl-L-tyrosine
264887-57-2

N-benzoxycarbonyl-L-valyl-O-benzyl-L-tyrosine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water at 20℃; Condensation;78%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

(S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol
85803-44-7

(S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 6h;77%
Stage #1: O-benzyl-S-tyrosine With sodium tetrahydroborate; iodine In tetrahydrofuran for 3h; Heating;
Stage #2: With potassium hydroxide In tetrahydrofuran; methanol at 20℃;		66%
Yield given. Multistep reaction;
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

sodium acetate
127-09-3

sodium acetate

(S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid
267228-34-2

(S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid

Conditions
ConditionsYield
With acetic acid; isopentyl nitrite at 20℃; for 72h;77%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

(S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid
162919-37-1

(S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid

Conditions
ConditionsYield
Stage #1: O-benzyl-S-tyrosine With sulfuric acid; sodium nitrite In tetrahydrofuran; water at 0 - 20℃; for 3h;
Stage #2: With water In tetrahydrofuran at 10 - 20℃;		76%
With sulfuric acid; sodium nitrite In water; N,N-dimethyl-formamide at 20℃; for 13h; Inert atmosphere;62%
Stage #1: O-benzyl-S-tyrosine With potassium hydrogensulfate In 1,4-dioxane; water at 0 - 5℃; for 1h;
Stage #2: With sodium nitrite In 1,4-dioxane; water at 30℃; for 4h; Product distribution / selectivity;		50%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

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

O-benzyl-S-tyrosine

N-Carboxy-O-benzyl-L-tyrosine Anhydride
22831-96-5

N-Carboxy-O-benzyl-L-tyrosine Anhydride

Conditions
ConditionsYield
Stage #1: O-benzyl-S-tyrosine With Pinene In ethyl acetate Inert atmosphere; Reflux;
Stage #2: bis(trichloromethyl) carbonate In ethyl acetate for 2h; Inert atmosphere; Reflux;		75%
Stage #1: O-benzyl-S-tyrosine With Pinene In ethyl acetate at 90℃; for 0.25h;
Stage #2: bis(trichloromethyl) carbonate at 90℃;
formaldehyd
50-00-0

formaldehyd

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

O-benzyl-S-tyrosine

(S)-3-(4-benzyloxyphenyl)-2-(dimethylamino)propanoic acid

(S)-3-(4-benzyloxyphenyl)-2-(dimethylamino)propanoic acid

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In water; acetonitrile at 22℃; for 1h; pH=Ca.7; Inert atmosphere;75%
phosgene
75-44-5

phosgene

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

O-benzyl-S-tyrosine

N-Carboxy-O-benzyl-L-tyrosine Anhydride
22831-96-5

N-Carboxy-O-benzyl-L-tyrosine Anhydride

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 50℃; for 1.5h;74.3%
In tetrahydrofuran; toluene at 50℃; for 1.5h;74.3%
In tetrahydrofuran; toluene at 50℃; for 1h;65%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

(4-(benzyloxy)phenyl)(5-(4-(benzyloxy)phenyl)thiazol-2-yl)methanone

(4-(benzyloxy)phenyl)(5-(4-(benzyloxy)phenyl)thiazol-2-yl)methanone

Conditions
ConditionsYield
With sodiumsulfide nonahydrate; water; iodine; acetic acid In dimethyl sulfoxide at 100℃; for 8h;73%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

O-benzyl-S-tyrosine

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

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Conditions
ConditionsYield
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
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

(4-(benzyloxy)phenyl)(5-(4-(benzyloxy)phenyl)oxazol-2-yl)methanone

(4-(benzyloxy)phenyl)(5-(4-(benzyloxy)phenyl)oxazol-2-yl)methanone

Conditions
ConditionsYield
With water; iodine; trifluoroacetic acid In dimethyl sulfoxide at 120℃; for 8h;66%
methanol
67-56-1

methanol

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

O-benzyl-S-tyrosine

O-benzyltyrosine methyl ester
57177-83-0

O-benzyltyrosine methyl ester

Conditions
ConditionsYield
With thionyl chloride at 40℃; for 4h; Esterification;64%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

zinc diacetate
557-34-6

zinc diacetate

[(C6H5CH2OC6H4CH2CH(NH2)COO)2Zn]

[(C6H5CH2OC6H4CH2CH(NH2)COO)2Zn]

Conditions
ConditionsYield
With sodium hydroxide In methanol; water addn. of soln. of PhCH2OC6H4CH2CH(NH2)CO2H in MeOH to aq. NaOH and Zn(OAc)2 (0.5 equiv.), stirring for 3 h at 50-60°C; removal of solvent, washing several times with Et2O, MeOH and H2O, elem.anal.;63%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

O-benzyl-S-tyrosine

Tyr(Bn)-tBu.HCl

Tyr(Bn)-tBu.HCl

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; O-benzyl-S-tyrosine With sodium hydrogencarbonate In tetrahydrofuran; water for 3h;
Stage #2: With tert-Butyl 2,2,2-trichloroacetimidate In tetrahydrofuran
Stage #3: With hydrogenchloride; trifluoroacetic acid In dichloromethane; water		60%
O-benzyl-S-tyrosine
16652-64-5

O-benzyl-S-tyrosine

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

(methoxycarbonyl)methyl 2-(bis(methoxycarbonylmethyl)-L-amino)-3-(4-(benzyloxy)phenyl)propionate
1022087-04-2

(methoxycarbonyl)methyl 2-(bis(methoxycarbonylmethyl)-L-amino)-3-(4-(benzyloxy)phenyl)propionate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In various solvent(s) at 108℃; for 16h;55%

O-Benzyl-L-tyrosine Chemical Properties

The molecular formula of O-Benzyl-L-tyrosine(16652-64-5) is C16H17NO3 and its formula weight is 271.31.
O-Benzyl-L-tyrosine(16652-64-5) has a melting point of  259 °C (dec.)(lit.).
The chemical synonyms of O-Benzyl-L-tyrosine(16652-64-5) are (S)-2-AMINO-3-(4'-BENZYLOXYPHENYL)PROPANOIC ACID;O-BENZYL-L-TYR;O-BENZYL-L-TYROSINE;TYROSINE(BZL)-OH;L-TYROSINE BENZYL ETHER;H-TYR(BZL)-OH;4-BENZYLOXY-L-PHENYLALANINE;D-O-Benzyltyrosine
The molecular structure of O-Benzyl-L-tyrosine(16652-64-5):

O-Benzyl-L-tyrosine Toxicity Data With Reference

RTECS#: CAS# 16652-64-5: None listed
LD50/LC50: RTECS: Not available. 
Carcinogenicity: O-BENZYL-L-TYROSINE, 99% - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.

O-Benzyl-L-tyrosine Safety Profile

Safety Statements  22-24/25
WGK Germany  3

O-Benzyl-L-tyrosine Specification

Chemical Stability: Stable under normal temperatures and pressures. 
Conditions to Avoid: Strong oxidants. 
Incompatibilities with Other Materials Not available 
Hazardous Decomposition Products Irritating and toxic fumes and gases. 
Hazardous Polymerization Hazardous Polymerization

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