O-Methyl-L-threonine supplier

Name
O-METHYL-L-THREONINE
EINECS
CAS No. 4144-02-9
Article Data9
CAS DataBase
Density 1.143 g/cm³
Solubility
Melting Point 214-216 °C
Formula C₅H₁₁NO₃
Boiling Point 248 °C at 760 mmHg
Molecular Weight 133.147
Flash Point 103.8 °C
Transport Information
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Butyricacid, 2-amino-3-methoxy-, L- (8CI);(2S,3R)-2-Amino-3-methoxybutanoic acid;L-O-Methylthreonine;H-Thr(Me)-OH;O-Methylthreonine;
PSA 72.55000
LogP 0.13350

Synthetic route

: 44975-87-3
N-formyl-O-methyl-Ls-threonine

: 4144-02-9
O-methyl-L-threonine

Conditions

Conditions	Yield
With hydrogen bromide

: (2S,3R)-2-Benzyloxycarbonylamino-3-methoxy-butyric acid; compound with dicyclohexyl-amine

: 4144-02-9
O-methyl-L-threonine

Conditions

Conditions	Yield
(i) ion-exchange resin + form>, EtOH, H2O, (ii) H2, Pd-C; Multistep reaction;

: 70561-63-6
Benzyloxycarbonyl-O-methyl-threonin

: 4144-02-9
O-methyl-L-threonine

Conditions

Conditions	Yield
With hydrogen; Pd-BaSO4

: 4144-14-3
methyl (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methoxybutanoate

: 4144-02-9
O-methyl-L-threonine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. LiOH / tetrahydrofuran 2: H2 / Pd/BaSO4 View Scheme

: 2076-53-1, 2076-57-5, 4144-02-9, 4385-90-4, 34223-42-2, 88642-93-7, 104195-79-1, 104195-80-4
O-methyl-DL-threonine

: 4144-02-9
O-methyl-L-threonine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid anhydride / 45 - 70 °C 2: brucine; ethanol 3: HBr View Scheme

: 6622-23-7, 7153-82-4, 7505-36-4, 44975-87-3
N-formyl-O-methyl-DL-threonine

: 4144-02-9
O-methyl-L-threonine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: brucine; ethanol 2: HBr View Scheme

: N-Boc-L-Thr(Me)-OMe

: 4144-02-9
O-methyl-L-threonine

Conditions

Conditions	Yield
With hydrogenchloride at 120℃; for 16h;
With hydrogenchloride In water at 110 - 120℃; for 16h;	143 mg

: perthamide C

A: 107-97-1
sarcosine

B: 4144-02-9
O-methyl-L-threonine

C: 7423-92-9
o-hydroxyl-phenylalanine

D: 6734-41-4
cis-4-methyl-(S)-proline

Conditions

Conditions	Yield
With hydrogenchloride; water at 130℃;

...Expand

: perthamide C

A: 4144-02-9
O-methyl-L-threonine

B: 56-84-8
L-Aspartic acid

C: 5753-30-0
erythro-β-hydroxy-D-aspartic acid

Conditions

Conditions	Yield
With hydrogenchloride; water at 160℃;

...Expand

: perthamide D

A: 4144-02-9
O-methyl-L-threonine

B: 56-84-8
L-Aspartic acid

C: 63-91-2
L-phenylalanine

D: 5753-30-0
erythro-β-hydroxy-D-aspartic acid

Conditions

Conditions	Yield
With hydrogenchloride; water at 160℃;

...Expand

: 48068-25-3
(2S,3R)-2-((tert-butoxycarbonyl)amino)-3-methoxybutanoic acid

: 4144-02-9
O-methyl-L-threonine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 2h;	572 mg

: 4144-02-9
O-methyl-L-threonine

: 79-22-1
methyl chloroformate

: 1007881-21-1
(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid

Conditions

Conditions	Yield
Stage #1: O-methyl-L-threonine; methyl chloroformate With sodium hydroxide In water at 0℃; Stage #2: With hydrogenchloride In water pH=1;	97%
Stage #1: O-methyl-L-threonine; methyl chloroformate With sodium hydroxide In water at 0℃; Stage #2: With hydrogenchloride In water pH=1;	97%
With sodium hydroxide In water at 0℃; for 12h;	97%

: 4144-02-9
O-methyl-L-threonine

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-methyl-L-threonine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetonitrile for 2h;	95%
With sodium carbonate In 1,4-dioxane; water for 22h;	60%

: 4144-02-9
O-methyl-L-threonine

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

: 48068-25-3
(2S,3R)-2-((tert-butoxycarbonyl)amino)-3-methoxybutanoic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 18h;	94%
With sodium hydrogencarbonate

: 4144-02-9
O-methyl-L-threonine

: 72-19-5
L-threonine

Conditions

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 0 - 5℃;	67%
With hydrogen bromide

: 4144-02-9
O-methyl-L-threonine

: 1246891-52-0
(2R,3R)-2-amino-3-methoxybutan-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Inert atmosphere; Reflux;	55%
With diborane In tetrahydrofuran at 20 - 30℃; for 12h;

: 5177-27-5
5-amino-2,4-dichloropyrimidine

: 4144-02-9
O-methyl-L-threonine

: (7S)-2-chloro-7-((R)-1-methoxyethyl)-7,8-dihydropteridin-6(5H)-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃; for 16h;	54%

: 4144-02-9
O-methyl-L-threonine

: 26839-91-8, 26839-93-0, 67819-23-2, 104195-77-9, 104195-78-0, 120329-56-8
(2S,3R)-2-bromo-3-methoxy-butyric acid

Conditions

Conditions	Yield
With sulfuric acid; potassium bromide; sodium nitrite

: 4144-02-9
O-methyl-L-threonine

: 1147550-11-5
ammonium thiocyanate

: 108-24-7
acetic anhydride

: (S)-3-acetyl-5-((R)-1-methoxy-ethyl)-2-thioxo-imidazolidin-4-one

Conditions

Conditions	Yield
With acetic acid

...Expand

: 4144-02-9
O-methyl-L-threonine

: (E)-(S)-4-[((2S,3R)-2-tert-Butoxycarbonylamino-3-methoxy-butyryl)-methyl-amino]-2,5-dimethyl-hex-2-enoic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaHCO3 2: PyBOP; DIEA / CH2Cl2 View Scheme

: 4144-02-9
O-methyl-L-threonine

: (E)-(S)-4-{[(2S,3R)-3-Methoxy-2-((S)-3-methyl-2-methylamino-3-phenyl-butyrylamino)-butyryl]-methyl-amino}-2,5-dimethyl-hex-2-enoic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: aq. NaHCO3 2: PyBOP; DIEA / CH2Cl2 3: HCl / dioxane 4: PyBOP; DIEA / CH2Cl2 5: aq. LiOH / methanol 6: Acid hydrolysis View Scheme

: 4144-02-9
O-methyl-L-threonine

: (E)-(S)-4-[((2S,3R)-2-Amino-3-methoxy-butyryl)-methyl-amino]-2,5-dimethyl-hex-2-enoic acid ethyl ester; hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaHCO3 2: PyBOP; DIEA / CH2Cl2 3: HCl / dioxane View Scheme

: 4144-02-9
O-methyl-L-threonine

: (E)-(S)-4-({(2S,3R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-methoxy-butyryl}-methyl-amino)-2,5-dimethyl-hex-2-enoic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. NaHCO3 2: PyBOP; DIEA / CH2Cl2 3: HCl / dioxane 4: PyBOP; DIEA / CH2Cl2 5: aq. LiOH / methanol View Scheme

: 4144-02-9
O-methyl-L-threonine

: (E)-(S)-4-({(2S,3R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-methoxy-butyryl}-methyl-amino)-2,5-dimethyl-hex-2-enoic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. NaHCO3 2: PyBOP; DIEA / CH2Cl2 3: HCl / dioxane 4: PyBOP; DIEA / CH2Cl2 View Scheme

: 4144-02-9
O-methyl-L-threonine

: 5405-44-7
O3-methyl-4-deoxy-D-threonic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous sulfuric acid; sodium nitrite; potassium bromide 2: water; silver oxide View Scheme

: 4144-02-9
O-methyl-L-threonine

: 139601-90-4
(1-fluoro-2,4-dinitrophenyl)-5-L-alaninamide

: C14H18FN5O7

Conditions

Conditions	Yield
With triethylamine In acetone; acetonitrile at 70℃;

: 4144-02-9
O-methyl-L-threonine

: 1007881-21-1
(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid

Conditions

Conditions	Yield
	0.28 g (20%)

: 4144-02-9
O-methyl-L-threonine

: methyl ((1S,2R)-2-methoxy-1-(((2S)-2-(4-(2'-(2-((2S)-1-(N-(methoxycarbonyl)-O-methyl-L-threonyl-)-2-pyrrolidinyl)-1H-imidazol-4-yl)-5,5'-bi-thiazol-2-yl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate trifluoroacetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 0 °C 1.2: pH 1 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 3 h / 20 °C View Scheme

: 4144-02-9
O-methyl-L-threonine

: methyl ((1S,2R)-2-methoxy-1-(((2S)-2-(4-(5'-(2-((2S)-1-(N-(methoxycarbonyl)-O-methyl-L-threonyl-)-2-pyrrolidinyl)-1H-imidazol-4-yl)-2,2'-bi-1,3-thiazol-5-yl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate trifluoroacetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 0 °C 1.2: pH 1 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C View Scheme

: 4144-02-9
O-methyl-L-threonine

: C12H16N4O5

: C17H25N5O8

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetone at 40℃; for 1h;

: 4144-02-9
O-methyl-L-threonine

: 1415120-17-0
dimethyl ((2S,2'S,3R,3'R)-((2S,2'S,3aS,3a'S,7aS,7a'S)-2,2'-(5,5'-(tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaene-5,11-diyl)bis(1H-benzo[d]imidazole-5,2-diyl))bis(octahydro-1H-indole-2,1-diyl))bis(3-methoxy-1-oxobutane-2,1-diyl))dicarbamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / 1,4-dioxane / 16 h / 0 - 20 °C 1.2: pH 2 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 0 - 20 °C View Scheme

O-Methyl-L-threonine Specification

The L-Threonine, O-methyl-, with the CAS registry number 4144-02-9, is also known as (S)-2-Amino-3-methoxy-butyric acid. It belongs to the product categories of Threonine [Thr, T]; Amino Acids and Derivatives; Amino Acids and Derivatives. This chemical's molecular formula is C₅H₁₁NO₃ and molecular weight is 133.15. Its systematic name is called O-methyl-L-threonine. When you are using this chemical, please be cautious about it. You should not breathe its dust. Besides, you must avoid contacting it with skin and eyes.

Physical properties of L-Threonine, O-methyl-: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 4; (6)#H bond donors: 3; (7)#Freely Rotating Bonds: 4; (8)Index of Refraction: 1.461; (9)Molar Refractivity: 31.97 cm³; (10)Molar Volume: 116.4 cm³; (11)Surface Tension: 41.8 dyne/cm; (12)Density: 1.143 g/cm³; (13)Flash Point: 103.8 °C; (14)Enthalpy of Vaporization: 53.42 kJ/mol; (15)Boiling Point: 248 °C at 760 mmHg; (16)Vapour Pressure: 0.008 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: OC(=O)[C@@H](N)C(C)OC
(2)InChI: InChI=1/C5H11NO3/c1-3(9-2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t3?,4-/m0/s1
(3)InChIKey: FYCWLJLGIAUCCL-BKLSDQPFBW

Product Name

O-METHYL-L-THREONINE

Synthetic route

O-Methyl-L-threonine Specification

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