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123715-02-6

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123715-02-6 Usage

Uses

L-2'',6''-Dimethyltyrosine (Dmt) enhances receptor affinity, functional bioactivity and in vivo analgesia of opioid peptides.

Check Digit Verification of cas no

The CAS Registry Mumber 123715-02-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,3,7,1 and 5 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 123715-02:
(8*1)+(7*2)+(6*3)+(5*7)+(4*1)+(3*5)+(2*0)+(1*2)=96
96 % 10 = 6
So 123715-02-6 is a valid CAS Registry Number.

123715-02-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid

1.2 Other means of identification

Product number -
Other names 2,6-dimethyl-L-tyrosine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123715-02-6 SDS

123715-02-6Synthetic route

C44H50N2O8
1185756-58-4

C44H50N2O8

Conditions
ConditionsYield
With hydrogen iodide for 3h; Reflux;100%
C21H30N2O4S

C21H30N2O4S

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water at 0℃; for 3h;94.8%
O-ethoxy-2,6-dimethyl-L-tyrosine

O-ethoxy-2,6-dimethyl-L-tyrosine

Conditions
ConditionsYield
With hydrogen iodide for 4h; Reagent/catalyst; Reflux;91%
(S)-N-Boc-2,6-dimethyltyrosine
99953-00-1

(S)-N-Boc-2,6-dimethyltyrosine

Conditions
ConditionsYield
With hydrogenchloride In water83%
(2S)-2-amino-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-(4-hydroxy-2,6-dimethylphenyl)propan-1-one

(2S)-2-amino-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-(4-hydroxy-2,6-dimethylphenyl)propan-1-one

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran at 0℃; for 1h;82%
C34H32ClN3NiO4

C34H32ClN3NiO4

A

(R)-N-(2-benzoyl-4-chlorophenyl)-2-((1-phenylethyl)amino)acetamide
1616506-47-8

(R)-N-(2-benzoyl-4-chlorophenyl)-2-((1-phenylethyl)amino)acetamide

B

H-Dmt
123715-02-6

H-Dmt

Conditions
ConditionsYield
With hydrogenchloride In methanol at 50℃; for 4h;A n/a
B 75.1%
N-Acetyl-2,6 dimethyl-O-methyl-(S)-tyrosine methyl ester
126312-59-2

N-Acetyl-2,6 dimethyl-O-methyl-(S)-tyrosine methyl ester

Conditions
ConditionsYield
With hydrogen bromide Heating;
1-iodo-2,6-dimethyl-4-methoxybenzene
90609-47-5

1-iodo-2,6-dimethyl-4-methoxybenzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / Pd(OAc)2, tri-o-tolylphosphine / acetonitrile / Heating
2: H2 / BF4 / ethyl acetate / 60 °C
3: 48percent HBr / Heating
View Scheme
Methyl-(Z)-α-acetamido-β-(2,6-dimethyl-4methoxyphenyl) acrylate
126312-58-1

Methyl-(Z)-α-acetamido-β-(2,6-dimethyl-4methoxyphenyl) acrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / BF4 / ethyl acetate / 60 °C
2: 48percent HBr / Heating
View Scheme
N-acetyl-2,6-dimethyl-DL-tyrosine
1255098-61-3

N-acetyl-2,6-dimethyl-DL-tyrosine

A

(R)-N-acetyl-2,6-dimethyltyrosine
1310488-05-1

(R)-N-acetyl-2,6-dimethyltyrosine

B

H-Dmt
123715-02-6

H-Dmt

Conditions
ConditionsYield
With acylase I from porcine kidney; cobalt(II) chloride; sodium hydroxide at 40℃; for 24h; pH=8; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
(S)-N-acetyl-2,6-dimethyltyrosine
1333148-31-4

(S)-N-acetyl-2,6-dimethyltyrosine

Conditions
ConditionsYield
With hydrogenchloride; acylase I from porcine kidney at 35℃; for 72h; pH=8; Enzymatic reaction; enantioselective reaction;
4-iodo-3,5-dimethylphenol
80826-86-4

4-iodo-3,5-dimethylphenol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridine / 10 °C
1.2: 39 - 55 °C / Large scale reaction
2.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine
3.1: [Rh(1,5-COD)(S,S-Et-FerroTANE)]BF4; hydrogen / ethyl acetate / 16 h / 60 °C / 3750.38 Torr
4.1: hydrogenchloride; water / 30 - 90 °C
4.2: 40 - 47 °C / pH 4
View Scheme
Multi-step reaction with 5 steps
1.1: pyridine / 10 °C
1.2: 39 - 55 °C / Large scale reaction
2.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine
3.1: [Rh(1,5-COD)(S,S-Et-FerroTANE)]BF4; hydrogen / ethyl acetate / 16 h / 60 °C / 3750.38 Torr
4.1: cobalt(II) chloride; sodium hydroxide / 35 °C / pH 8 - 10 / aq. phosphate buffer
5.1: hydrogenchloride; acylase I from porcine kidney / 72 h / 35 °C / pH 8 / Enzymatic reaction
View Scheme
3,5-dimethyl-4-iodophenol acetate
145235-84-3

3,5-dimethyl-4-iodophenol acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine
2.1: [Rh(1,5-COD)(S,S-Et-FerroTANE)]BF4; hydrogen / ethyl acetate / 16 h / 60 °C / 3750.38 Torr
3.1: hydrogenchloride; water / 30 - 90 °C
3.2: 40 - 47 °C / pH 4
View Scheme
Multi-step reaction with 4 steps
1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine
2: [Rh(1,5-COD)(S,S-Et-FerroTANE)]BF4; hydrogen / ethyl acetate / 16 h / 60 °C / 3750.38 Torr
3: cobalt(II) chloride; sodium hydroxide / 35 °C / pH 8 - 10 / aq. phosphate buffer
4: hydrogenchloride; acylase I from porcine kidney / 72 h / 35 °C / pH 8 / Enzymatic reaction
View Scheme
methyl (Z)-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-2-propenoate
145235-85-4

methyl (Z)-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-2-propenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: [Rh(1,5-COD)(S,S-Et-FerroTANE)]BF4; hydrogen / ethyl acetate / 16 h / 60 °C / 3750.38 Torr
2.1: hydrogenchloride; water / 30 - 90 °C
2.2: 40 - 47 °C / pH 4
View Scheme
Multi-step reaction with 3 steps
1: [Rh(1,5-COD)(S,S-Et-FerroTANE)]BF4; hydrogen / ethyl acetate / 16 h / 60 °C / 3750.38 Torr
2: cobalt(II) chloride; sodium hydroxide / 35 °C / pH 8 - 10 / aq. phosphate buffer
3: hydrogenchloride; acylase I from porcine kidney / 72 h / 35 °C / pH 8 / Enzymatic reaction
View Scheme
(S)-4-acetoxy-N-acetyl-2,6-dimethylphenylalanine methyl ester
145235-86-5

(S)-4-acetoxy-N-acetyl-2,6-dimethylphenylalanine methyl ester

Conditions
ConditionsYield
Stage #1: (S)-4-acetoxy-N-acetyl-2,6-dimethylphenylalanine methyl ester With hydrogenchloride; water at 30 - 90℃;
Stage #2: With sodium hydroxide In water at 40 - 47℃; pH=4;
Multi-step reaction with 2 steps
1: cobalt(II) chloride; sodium hydroxide / 35 °C / pH 8 - 10 / aq. phosphate buffer
2: hydrogenchloride; acylase I from porcine kidney / 72 h / 35 °C / pH 8 / Enzymatic reaction
View Scheme
3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride; potassium iodate; potassium iodide / methanol; water / 0 - 20 °C / Large scale reaction
2.1: pyridine / 10 °C
2.2: 39 - 55 °C / Large scale reaction
3.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine
4.1: [Rh(1,5-COD)(S,S-Et-FerroTANE)]BF4; hydrogen / ethyl acetate / 16 h / 60 °C / 3750.38 Torr
5.1: hydrogenchloride; water / 30 - 90 °C
5.2: 40 - 47 °C / pH 4
View Scheme
Multi-step reaction with 6 steps
1.1: hydrogenchloride; potassium iodate; potassium iodide / methanol; water / 0 - 20 °C / Large scale reaction
2.1: pyridine / 10 °C
2.2: 39 - 55 °C / Large scale reaction
3.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine
4.1: [Rh(1,5-COD)(S,S-Et-FerroTANE)]BF4; hydrogen / ethyl acetate / 16 h / 60 °C / 3750.38 Torr
5.1: cobalt(II) chloride; sodium hydroxide / 35 °C / pH 8 - 10 / aq. phosphate buffer
6.1: hydrogenchloride; acylase I from porcine kidney / 72 h / 35 °C / pH 8 / Enzymatic reaction
View Scheme
Multi-step reaction with 5 steps
1.1: triethylamine / dichloromethane / 1 h / 20 °C
2.1: zinc(II) chloride; chlorosulfonic acid / 0.5 h / -10 °C
2.2: 2 h / 5 - 10 °C
3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
3.2: 3 h / -78 - 20 °C / Inert atmosphere
4.1: hydrogenchloride / tetrahydrofuran; water / 4 h / 0 °C
5.1: lithium hydroxide / tetrahydrofuran / 1 h / 0 °C
View Scheme
FMoc-L-2,6-dimethyltyrosine

FMoc-L-2,6-dimethyltyrosine

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 20℃; for 2.33333h;4.3 g
1-((4-bromo-3,5-dimethylphenoxy)methyl)benzene
95741-44-9

1-((4-bromo-3,5-dimethylphenoxy)methyl)benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: magnesium / tetrahydrofuran / 6 h / 25 °C / Reflux
1.2: 25 °C
2.1: methanol / 5 h / 25 °C
3.1: sodium periodate / tetrachloromethane; acetonitrile; water / 5 h
4.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 2068.65 Torr
View Scheme
(2R,3S)-1,2-isopropylidene-3-(tert-butoxycarbonyl)amino-4-[(4-benzyloxy-2,6-dimethyl)phenyl]butane-1,2-diol

(2R,3S)-1,2-isopropylidene-3-(tert-butoxycarbonyl)amino-4-[(4-benzyloxy-2,6-dimethyl)phenyl]butane-1,2-diol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol / 5 h / 25 °C
2: sodium periodate / tetrachloromethane; acetonitrile; water / 5 h
3: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 2068.65 Torr
View Scheme
(S)-O-benzyl-N-(tert-butoxycarbonyl)-2,6-dimethyltyrosine
945669-52-3

(S)-O-benzyl-N-(tert-butoxycarbonyl)-2,6-dimethyltyrosine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol under 2068.65 Torr; for 24h;
3,5-Dimethylphenyl ethyl carbonate
26177-58-2

3,5-Dimethylphenyl ethyl carbonate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: zinc(II) chloride; chlorosulfonic acid / 0.5 h / -10 °C
1.2: 2 h / 5 - 10 °C
2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
2.2: 3 h / -78 - 20 °C / Inert atmosphere
3.1: hydrogenchloride / tetrahydrofuran; water / 4 h / 0 °C
4.1: lithium hydroxide / tetrahydrofuran / 1 h / 0 °C
View Scheme
O-ethoxycarbonyl-3,5-dimethyl-4-chloromethylphenol
54373-50-1

O-ethoxycarbonyl-3,5-dimethyl-4-chloromethylphenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
1.2: 3 h / -78 - 20 °C / Inert atmosphere
2.1: hydrogenchloride / tetrahydrofuran; water / 4 h / 0 °C
3.1: lithium hydroxide / tetrahydrofuran / 1 h / 0 °C
View Scheme
benzyl chloroformate
501-53-1

benzyl chloroformate

2,6-dimethyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine
137764-59-1

2,6-dimethyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine

Conditions
ConditionsYield
With sodium hydroxide for 16h;70%
Stage #1: H-Dmt With sodium hydrogencarbonate In 1,4-dioxane; water for 0.166667h;
Stage #2: benzyl chloroformate In 1,4-dioxane; water at 20℃; for 2h;
6 g
isobutyl chloroformate
543-27-1

isobutyl chloroformate

C16H23NO5

C16H23NO5

Conditions
ConditionsYield
With 4-methyl-morpholine In tetrahydrofuran at -23℃; for 0.75h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-N-Boc-2,6-dimethyltyrosine
99953-00-1

(S)-N-Boc-2,6-dimethyltyrosine

Conditions
ConditionsYield
With sodium hydroxide In tert-butyl alcohol at 0 - 20℃; for 27h;
With triethylamine
Stage #1: di-tert-butyl dicarbonate; H-Dmt With water; sodium hydroxide at 20℃; for 72h; pH=8 - 10;
Stage #2: With hydrogenchloride In water; ethyl acetate for 0.166667h; pH=4;
689 g
methanol
67-56-1

methanol

(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester
928195-92-0

(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride In methanol
(2S,3S)-β-methylcyclohexylalanine
925672-53-3

(2S,3S)-β-methylcyclohexylalanine

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

N-tert-butoxycarbonyl-L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

2-[2-({2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-cyclohexyl-butyrylamino]-3-phenyl-propionic acid

2-[2-({2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-cyclohexyl-butyrylamino]-3-phenyl-propionic acid

Conditions
ConditionsYield
Multistep reaction;
(2S,3S)-β-methylcyclohexylalanine
925672-53-3

(2S,3S)-β-methylcyclohexylalanine

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

N-tert-butoxycarbonyl-L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [1-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyl-propyl]-amide

2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [1-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyl-propyl]-amide

Conditions
ConditionsYield
Multistep reaction;
(2R,3S)-β-methylcyclohexylalanine

(2R,3S)-β-methylcyclohexylalanine

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

N-tert-butoxycarbonyl-L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

2-[2-({2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-cyclohexyl-butyrylamino]-3-phenyl-propionic acid

2-[2-({2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-cyclohexyl-butyrylamino]-3-phenyl-propionic acid

Conditions
ConditionsYield
Multistep reaction;
(2R,3S)-β-methylcyclohexylalanine

(2R,3S)-β-methylcyclohexylalanine

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

N-tert-butoxycarbonyl-L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [1-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyl-propyl]-amide

2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [1-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyl-propyl]-amide

Conditions
ConditionsYield
Multistep reaction;
(2S,3R)-β-methylcyclohexylalanine

(2S,3R)-β-methylcyclohexylalanine

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

N-tert-butoxycarbonyl-L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

2-[2-({2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-cyclohexyl-butyrylamino]-3-phenyl-propionic acid

2-[2-({2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-cyclohexyl-butyrylamino]-3-phenyl-propionic acid

Conditions
ConditionsYield
Multistep reaction;
(2S,3R)-β-methylcyclohexylalanine

(2S,3R)-β-methylcyclohexylalanine

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

N-tert-butoxycarbonyl-L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [1-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyl-propyl]-amide

2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [1-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyl-propyl]-amide

Conditions
ConditionsYield
Multistep reaction;
(2R,3R)-β-methylcyclohexylalanine
925672-54-4

(2R,3R)-β-methylcyclohexylalanine

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

N-tert-butoxycarbonyl-L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

2-[2-({2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-cyclohexyl-butyrylamino]-3-phenyl-propionic acid

2-[2-({2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-cyclohexyl-butyrylamino]-3-phenyl-propionic acid

Conditions
ConditionsYield
Multistep reaction;
(2R,3R)-β-methylcyclohexylalanine
925672-54-4

(2R,3R)-β-methylcyclohexylalanine

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

N-tert-butoxycarbonyl-L-phenylalanine

L-Tic-OH
74163-81-8

L-Tic-OH

2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [1-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyl-propyl]-amide

2-[2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [1-(1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyl-propyl]-amide

Conditions
ConditionsYield
Multistep reaction;
methanol
67-56-1

methanol

(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester; hydrochloride

(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester; hydrochloride

Conditions
ConditionsYield
Stage #1: H-Dmt With thionyl chloride
Stage #2: methanol Further stages.;
H-Dmt-NH2
331283-95-5

H-Dmt-NH2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: SOCl2 / methanol
2: Et3N
3: NH3 / methanol
4: HCl / dioxane
View Scheme
2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-methoxy-propionamide

2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-methoxy-propionamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: HCl / dioxane
View Scheme
H-Dmt-NH-CH3

H-Dmt-NH-CH3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: HCl / dioxane
View Scheme
(S)-2-Dimethylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

(S)-2-Dimethylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: SOCl2 / methanol
2: Et3N
3: NH3 / methanol
4: HCl / dioxane
5: NaBH3CN / dioxane
View Scheme
2-amino-N-hydroxy-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

2-amino-N-hydroxy-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: NH2OH
3: HCl / dioxane
View Scheme
2-amino-N-ethyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

2-amino-N-ethyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: HCl / dioxane
View Scheme
2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-isopropyl-propionamide

2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-isopropyl-propionamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: HCl / dioxane
View Scheme
2-amino-N-aminomethyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

2-amino-N-aminomethyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: HCl / dioxane
View Scheme
2-amino-N-tert-butyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

2-amino-N-tert-butyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: HCl / dioxane
View Scheme
2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-propyl-propionamide

2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-propyl-propionamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: PyBOP; N,N-diisopropylethylamine
3: HCl / dioxane
View Scheme

123715-02-6Relevant articles and documents

An Efficient and Highly Asymmetric Synthesis of (S)-2’,6’-Dimethyltyrosine

He, Kailun,Zhu, Fangmeng,Li, Hua,Tang, Jian,Zhang, Xingxian

, p. 510 - 516 (2020)

-

Preparation method of 2,6-dimethyl-L-tyrosine

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Paragraph 0056-0066, (2019/01/05)

The invention discloses a preparation method of 2,6-dimethyl-L-tyrosine. The preparation method comprises the steps as follows: halide is added to an organic solvent and subjected to an SN2 nucleophilic addition reaction with L-camphor glycinate under the alkaline condition to produce a chiral compound (III); a compound (IV) is obtained after removal of a chiral auxiliary group from the compound (III); the target compound 2,6-dimethyl-L-tyrosine is obtained after removal of a protecting group from the compound (IV). The method has the characteristics that raw materials are cheap and easy to obtain, the reaction route is short, the operation is convenient, the yield and the stereoselectivity are high and the like, and the method has higher industrial application and economic value.

PROCESSES FOR PREPARING PHARMACEUTICALLY RELEVANT PEPTIDES

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Paragraph 0155, (2016/09/26)

The present technology provides methods of generating the peptides, and pharmaceutically acceptable salts of the peptides and intermediates thereof. In some embodiments, the peptide is D-Arg-2′6′-Dmt-Lys-Phe-NH2.

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