123715-02-6

Basic information

• Product Name: 2,6-Dimethyl-L-tyrosine
• Synonyms: (S)-2',6'-dimethyl tyrosine;(S)-2-Amino-3-(4-hydroxy-2,6-dimethylphenyl)propionic acid;2,6-Dimethyl-L-tyrosine;L-Tyrosine, 2,6-dimethyl-;(S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid;L-2',6'-DiMethyltyrosine;(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid
• CAS NO: 123715-02-6
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.24
• Product Categories: pharmacetical;Benzene series;API intermediates;Non-natural amino acids
• Mol File: 123715-02-6.mol

Chemical Properties

• Melting Point: 239-240 °C (decomp)
• Boiling Point: 412.758 °C at 760 mmHg
• Flash Point: 203.429 °C
• Appearance: /
• Density: 1.242 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.34±0.20(Predicted)
• CAS DataBase Reference: 2,6-Dimethyl-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethyl-L-tyrosine(123715-02-6)
• EPA Substance Registry System: 2,6-Dimethyl-L-tyrosine(123715-02-6)

Safety Data

• Hazardous Substances Data: 123715-02-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dimethyl-L-tyrosine is used as a building block for the development of opioid peptides, which are crucial in the treatment of pain management. Its incorporation into these peptides enhances their receptor affinity, leading to improved functional bioactivity and increased in vivo analgesic effects. This makes Dmt a valuable component in the design and synthesis of novel pain-relieving drugs.
Used in Pain Management:
2,6-Dimethyl-L-tyrosine is used as an enhancer for opioid peptides in pain management applications. By improving the receptor affinity and bioactivity of these peptides, Dmt contributes to the development of more effective analgesic agents. This can potentially lead to better pain relief and improved quality of life for patients suffering from various types of pain, including chronic and acute conditions.

Synthetic route

C44H50N2O8 (1185756-58-4) → H-Dmt (123715-02-6)

Conditions	Yield
With hydrogen iodide for 3h; Reflux;	100%

C21H30N2O4S → H-Dmt (123715-02-6)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water at 0℃; for 3h;	94.8%

O-ethoxy-2,6-dimethyl-L-tyrosine → H-Dmt (123715-02-6)

Conditions	Yield
With hydrogen iodide for 4h; Reagent/catalyst; Reflux;	91%

(S)-N-Boc-2,6-dimethyltyrosine (99953-00-1) → H-Dmt (123715-02-6)

Conditions	Yield
With hydrogenchloride In water	83%

(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 → H-Dmt (123715-02-6)

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

C34H32ClN3NiO4 → (R)-N-(2-benzoyl-4-chlorophenyl)-2-((1-phenylethyl)amino)acetamide (1616506-47-8) + H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
With hydrogen bromide Heating;

1-iodo-2,6-dimethyl-4-methoxybenzene (90609-47-5) → H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
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) → (R)-N-acetyl-2,6-dimethyltyrosine (1310488-05-1) + H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
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 → H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
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 → H-Dmt (123715-02-6)

Conditions	Yield
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) → H-Dmt (123715-02-6)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol under 2068.65 Torr; for 24h;

3,5-Dimethylphenyl ethyl carbonate (26177-58-2) → H-Dmt (123715-02-6)

Conditions

Yield

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) → H-Dmt (123715-02-6)

Conditions	Yield
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) + H-Dmt (123715-02-6) → 2,6-dimethyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine (137764-59-1)

Conditions	Yield
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

H-Dmt (123715-02-6) + isobutyl chloroformate (543-27-1) → C16H23NO5

Conditions	Yield
With 4-methyl-morpholine In tetrahydrofuran at -23℃; for 0.75h;

di-tert-butyl dicarbonate (24424-99-5) + H-Dmt (123715-02-6) → (S)-N-Boc-2,6-dimethyltyrosine (99953-00-1)

Conditions	Yield
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) + H-Dmt (123715-02-6) → (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester (928195-92-0)

Conditions	Yield
With thionyl chloride In methanol

(2S,3S)-β-methylcyclohexylalanine (925672-53-3) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + L-Tic-OH (74163-81-8) + H-Dmt (123715-02-6) → 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	Yield
Multistep reaction;

(2S,3S)-β-methylcyclohexylalanine (925672-53-3) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + L-Tic-OH (74163-81-8) + H-Dmt (123715-02-6) → 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	Yield
Multistep reaction;

(2R,3S)-β-methylcyclohexylalanine + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + L-Tic-OH (74163-81-8) + H-Dmt (123715-02-6) → 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	Yield
Multistep reaction;

(2R,3S)-β-methylcyclohexylalanine + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + L-Tic-OH (74163-81-8) + H-Dmt (123715-02-6) → 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	Yield
Multistep reaction;

(2S,3R)-β-methylcyclohexylalanine + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + L-Tic-OH (74163-81-8) + H-Dmt (123715-02-6) → 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	Yield
Multistep reaction;

(2S,3R)-β-methylcyclohexylalanine + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + L-Tic-OH (74163-81-8) + H-Dmt (123715-02-6) → 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	Yield
Multistep reaction;

(2R,3R)-β-methylcyclohexylalanine (925672-54-4) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + L-Tic-OH (74163-81-8) + H-Dmt (123715-02-6) → 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	Yield
Multistep reaction;

(2R,3R)-β-methylcyclohexylalanine (925672-54-4) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + L-Tic-OH (74163-81-8) + H-Dmt (123715-02-6) → 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	Yield
Multistep reaction;

methanol (67-56-1) + H-Dmt (123715-02-6) → (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester; hydrochloride

Conditions	Yield
Stage #1: H-Dmt With thionyl chloride Stage #2: methanol Further stages.;

H-Dmt (123715-02-6) → H-Dmt-NH2 (331283-95-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 / methanol 2: Et3N 3: NH3 / methanol 4: HCl / dioxane View Scheme

H-Dmt (123715-02-6) → 2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-methoxy-propionamide

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: HCl / dioxane View Scheme

H-Dmt (123715-02-6) → H-Dmt-NH-CH3

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: HCl / dioxane View Scheme

H-Dmt (123715-02-6) → (S)-2-Dimethylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions	Yield
Multi-step reaction with 5 steps 1: SOCl2 / methanol 2: Et3N 3: NH3 / methanol 4: HCl / dioxane 5: NaBH3CN / dioxane View Scheme

H-Dmt (123715-02-6) → 2-amino-N-hydroxy-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: NH2OH 3: HCl / dioxane View Scheme

H-Dmt (123715-02-6) → 2-amino-N-ethyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: HCl / dioxane View Scheme

H-Dmt (123715-02-6) → 2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-isopropyl-propionamide

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: HCl / dioxane View Scheme

H-Dmt (123715-02-6) → 2-amino-N-aminomethyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: HCl / dioxane View Scheme

H-Dmt (123715-02-6) → 2-amino-N-tert-butyl-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionamide

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: HCl / dioxane View Scheme

H-Dmt (123715-02-6) → 2-amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-propyl-propionamide

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

Upstream product

• 126312-59-2 N-Acetyl-2,6-dimethyl-O-methyl-(S)-tyrosine methyl ester 
• 90609-47-5 1-iodo-2,6-dimethyl-4-methoxybenzene 
• 126312-58-1 Methyl-(Z)-α-acetamido-β-(2,6-dimethyl-4methoxyphenyl) acrylate 
• 1185756-58-4 C₄₄H₅₀N₂O₈ 
• 1255098-61-3 N-acetyl-2,6-dimethyl-DL-tyrosine 
• 1333148-31-4 (S)-N-acetyl-2,6-dimethyltyrosine 
• 80826-86-4 4-iodo-3,5-dimethylphenol 
• 145235-84-3 4-iodo-3,5-dimethylphenyl acetate 
• 145235-85-4 methyl (Z)-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-2-propenoate 
• 145235-86-5 (S)-4-acetoxy-N-acetyl-2,6-dimethylphenylalanine methyl ester 
• 108-68-9 3,5-Dimethylphenol 
• 95741-44-9 1-((4-bromo-3,5-dimethylphenoxy)methyl)benzene 
• 99953-00-1 (S)-N-Boc-2,6-dimethyltyrosine 
• 945669-52-3 (S)-O-benzyl-N-(tert-butoxycarbonyl)-2,6-dimethyltyrosine 

Downstream Products

• 137764-59-1 2,6-dimethyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine 
• 99953-00-1 (S)-N-Boc-2,6-dimethyltyrosine 
• 928195-92-0 (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester 
• 928138-99-2 (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester; hydrochloride 
• 331283-95-5 H-Dmt-NH₂ 

Relevant articles and documents

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

The invention discloses a preparation method of 2, 6-dimethyl-L-tyrosine. The method includes: dissolving camphor sulfonamide shown as formula (I) in an organic solvent A, adding trimethylaluminum under the protection of nitrogen, and stirring the substances uniformly to obtain a mixed solution A, then dissolving diphenyl imine ester shown as formula (II) into an organic solvent B to obtain a mixed solution B, reacting the mixed solution A with the mixed solution B to obtain a chiral compound shown as formula (III), dissolving the chiral compound in an organic solvent C, adding a halide shownas formula (IV), under the protection of inert gas, carrying out nucleophilic substitution reaction to obtain a compound shown as formula (V), dissolving the compound shown as formula (V) in an organic solvent D, under the protection of acid, carrying out an imine hydrolysis reaction to obtain a compound shown as formula (VI), dissolving the compound shown as formula (VI) in an organic solvent E,and carrying out reaction under the action of an alkaline substance B, thus obtaining the 2, 6-dimethyl-L-tyrosine. The method provided by the invention has the advantages of cheap and easily available raw materials, short route, high yield and good stereoselectivity.

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

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.

Method for Preparing Unnatural Amino Acids

The present invention relates to a manufacturing method of unnatural amino acids and unnatural amino acids manufactured thereby. Specifically, the present invention relates to an asymmetric synthesis method which can manufacture unnatural amino acids having significantly high optical purity, and to the unnatural amino acids manufactured thereby. A manufacturing method of unnatural amino acids represented by chemical formula 6 or chemical formula 7 comprises the steps of: synthesizing a compound represented by chemical formula 4 or chemical formula 5; manufacturing a diol compound; and manufacturing a carboxylic acid compound.COPYRIGHT KIPO 2016

PROCESSES FOR PREPARING PHARMACEUTICALLY RELEVANT PEPTIDES

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.

Design and synthesis of (S)- and (R)-α-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of α-amino acids

This work presents the first chemical approach for the resolution of α-amino acids offering the following advantages: (1) The specially designed resolving reagent is derived from α-(phenyl)ethylamine, the most inexpensive chiral auxiliary, which can be re

Development of an asymmetric hydrogenation route to (S)- N -Boc-2,6-dimethyltyrosine

An improved, simpler and potentially more economical route to (S)-N-Boc-2,6-dimethyltyrosine 1, based on a previously published route, is presented. Key modifications were to prepare the dehydroaminoacid hydrogenation substrate 6 in a one-pot process directly from serine methyl ester and 4-iodo-3,5-dimethylphenyl acetate 4 and to identify a significantly more active asymmetric hydrogenation catalyst that allowed a 5-fold reduction in catalyst loading.

A highly efficient stereocontrolled synthesis of (S)-2′,6′-dimethyltyrosine [(S)-DMT]

A new, practical and very convenient stereocontrolled synthesis of (S)-2′,6′-dimethyltyrosine [(S)-Dmt] 4 was accomplished in a good yield, starting from the chiral synthon 1,4-N,N-[(S)-phenylethyl]-piperazine-2,5-dione 1. The procedure, which is an exten

A convenient asymmetric synthesis of the unnatural amino acid 2,6-dimethyl-L-tyrosine

The title compound was prepared in high optical purity by a five-step synthesis from 3,5-dimethylphenol on a kilogram scale. The key steps were a modified palladium-catalyzed coupling of an aryl iodide with methyl 2-acetamidoacrylate and hydrogenation of the resulting sterically hindered dehydroamino acid 4 using [Rh(1,5-COD)(R,R-DIPAMP)]BF4 as catalyst.