Methyl L-threoninate supplier

Name
L-THREONINE METHYL ESTER
EINECS 222-158-1
CAS No. 3373-59-9
Article Data43
CAS DataBase
Density 1.143 g/cm³
Solubility
Melting Point 213-214 °C
Formula C₅H₁₁NO₃
Boiling Point 238.58 °C at 760 mmHg
Molecular Weight 133.147
Flash Point 98.09 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Threonine methyl ester;NSC 287508;Methyl threoninate;MethylL-threoninate;Methyl 2(S):3(R)-threoninate;Threonine,methyl ester, L- (6CI,7CI,8CI);
PSA 72.55000
LogP -0.43220

Synthetic route

: 67-56-1
methanol

: 72-19-5
L-threonine

: 3373-59-9
L-threonine methyl ester

Conditions

Conditions	Yield
With thionyl chloride at 0℃; for 25h; Temperature; Reflux;	80%
With hydrogenchloride Heating;
With hydrogenchloride for 5h; Heating; Yield given;

: 60538-19-4, 79479-07-5, 96099-84-2, 113525-91-0
N-(tert-butoxycarbonyl)-l-threonine methyl ester

: 3373-59-9
L-threonine methyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 10 - 25℃; for 2h;	70%

: 67-56-1
methanol

: (3S,6R,1''S)-5-ethoxy-3-(1''-hydroxyethyl)-6-methyl-3,6-dihydro-1H-pyrazine-2-one

A: 3373-59-9, 53216-06-1, 68331-48-6, 79617-28-0, 82679-55-8, 118525-51-2
(2S,3S)-methyl 2-amino-3-hydroxybutanoate

B: 3373-59-9
L-threonine methyl ester

Conditions

Conditions	Yield
Multistep reaction;

...Expand

: 72-19-5
L-threonine

: 3373-59-9
L-threonine methyl ester

Conditions

Conditions	Yield
With thionyl chloride In methanol

: 3373-59-9
L-threonine methyl ester

: 76-83-5
trityl chloride

: 74481-55-3
methyl (2S,3R)-3-hydroxy-2-triphenylmethylaminobutanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In chloroform at 20℃; Alkylation; triphenylmethylation; tritylation;	89%

: 3373-59-9
L-threonine methyl ester

: 670233-20-2
(4S,5R)-4-[(Z)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-carboxy-but-1-enylcarbamoyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 670233-21-3
(4S,5R)-4-[(Z)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,2R)-2-hydroxy-1-methoxycarbonyl-propylcarbamoyl)-but-1-enylcarbamoyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine	100%

: 3373-59-9
L-threonine methyl ester

: 39994-75-7
L-threonine methyl ester hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 18h; Inert atmosphere;	100%

: 3373-59-9
L-threonine methyl ester

: 2937-50-0
Allyl chloroformate

: 221351-00-4
N-Allyloxycarbonyl-L-threonine methyl ester

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 18.5h; Substitution;	98%

: 60397-83-3
N-acetyl-(S)-alanine cyanomethyl ester

: 3373-59-9
L-threonine methyl ester

: C10H18N2O5

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran for 16h; Microwave irradiation;	98%

: 3373-59-9
L-threonine methyl ester

: 65635-85-0
N-methyl-N-(benzyloxycarbonyl)-D-leucine

: 120448-64-8
-threonine methyl ester

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane	97%

: 3373-59-9
L-threonine methyl ester

: 79-22-1
methyl chloroformate

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

Conditions

Conditions	Yield
With sodium hydroxide In water at 0℃; for 12h;	97%

: 3373-59-9
L-threonine methyl ester

: C8H9F6NO3

: C10H18N2O5

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran at 70℃; for 4h; Temperature; Microwave irradiation;	96%

: 3373-59-9
L-threonine methyl ester

: 98-88-4
benzoyl chloride

: 79893-89-3
N-benzoyl-L-threonine methyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 12h;	95%
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃;
With sodium hydrogencarbonate In 1,4-dioxane; water at 0℃;

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

: 3373-59-9
L-threonine methyl ester

: 60538-19-4, 79479-07-5, 96099-84-2, 113525-91-0
N-(tert-butoxycarbonyl)-l-threonine methyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane	95%
With sodium hydrogencarbonate In methanol; water at 20℃; for 20h;	92%
With triethylamine In dichloromethane
With triethylamine In water; acetonitrile at 0 - 20℃;	8.08 g
With triethylamine In methanol at 10 - 35℃;

: 3373-59-9
L-threonine methyl ester

: 18942-49-9
Boc-D-Phe-OH

: 73763-45-8
N-Boc-L-Phe-L-Thr-O-Me

Conditions

Conditions	Yield
Stage #1: Boc-D-Phe-OH With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: L-threonine methyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18h;	95%

: 38496-18-3
2,6-dichloropyridine-3-carboxylic acid

: 3373-59-9
L-threonine methyl ester

: (2S,3R)-N-[(2,6-dichloropyridin-3-yl)carbonyl]threonine methyl ester

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 5h; Inert atmosphere;	94%

: 3373-59-9
L-threonine methyl ester

: C7H10F3NO3

: C10H18N2O5

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran for 16h; Microwave irradiation;	94%

: 3373-59-9
L-threonine methyl ester

: 42533-12-0
Z(OMe)-Lys(Z)-OH

: Z(OMe)-Lys(Z)-Thr-OMe

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane	93%
With dicyclohexyl-carbodiimide

: 104115-44-8
(2-oxocyclopent)acetic acid

: 3373-59-9
L-threonine methyl ester

: 1240492-81-2
(2R,3S,5aR,8aS)-2-methyl-4-oxo-octahydro-1-oxa-3a-aza-cyclopenta[c]pentalene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
at 110℃; under 11251.1 Torr; Meyer synthesis; Microwave irradiation; optical yield given as %de;	93%

: 3373-59-9
L-threonine methyl ester

: C8H10F5NO3

: C10H18N2O5

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran for 16h; Microwave irradiation;	93%

: 3373-59-9
L-threonine methyl ester

: 1596377-01-3
1-benzotriazolyl 3β-hydroxyolean-12-en-28-oate

: C35H57NO5

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h;	93%

: 3373-59-9
L-threonine methyl ester

: 1138-80-3
N-(Benzyloxycarbonyl)glycine

: 41961-03-9
Cbz-Gly-L-Thr-OMe

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide	92%
Stage #1: N-(Benzyloxycarbonyl)glycine With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: L-threonine methyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18h;	86%
With Sephadex G-50; triethylamine; bromelain In ethyl acetate at 37℃; for 7h;	50%

: 3373-59-9
L-threonine methyl ester

: 5333-86-8
ethyl benzimidate hydrochloride

: 60538-17-2, 62107-40-8, 74272-77-8, 79952-14-0, 79952-15-1, 82659-84-5, 88336-08-7
(4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	92%
In chloroform for 12h; Heating;	85%

: 15761-38-3
L-N-Boc-Ala

: 3373-59-9
L-threonine methyl ester

: 41938-15-2
methyl (tert-butoxycarbonyl)-L-alanyl-L-threoninate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In ethyl acetate Acylation;	92%
Stage #1: L-N-Boc-Ala With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.75h; Stage #2: L-threonine methyl ester With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	82%

: 3373-59-9
L-threonine methyl ester

: 160821-18-1
(4S,5R)-3-((benzyloxy)carbonyl)-2,2,5-trimethyloxazolidine-4-carboxylic acid

: 670233-30-4
(4S,5R)-4-((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propylcarbamoyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide	92%

: 3373-59-9
L-threonine methyl ester

: 66863-43-2
(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

: 900865-75-0
(S)-tert-butyl 3-((2S)-3-hydroxy-1-methoxy-1-oxobutan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h;	92%
Stage #1: (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid With benzotriazol-1-ol In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: L-threonine methyl ester With 4-methyl-morpholine; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h;	87%

: 3373-59-9
L-threonine methyl ester

: (2R,3R)-2-Benzyloxycarbonylamino-3-phenyl-pent-4-enoic acid

: (2S,3R)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-pent-4-enoylamino)-3-hydroxy-butyric acid methyl ester

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; triethylamine In dichloromethane	90.2%

: 495-69-2
Hippuric Acid

: 3373-59-9
L-threonine methyl ester

: 115494-73-0
Bz-Gly-Thr-OMe

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide	90%

: C15H18N2O5

: 3373-59-9
L-threonine methyl ester

: 1126476-83-2
(R/S)-tert-butyl-5-((2S,3R)-3-hydroxy-1-methoxy-1-oxobutan-2-ylcarbamoyl)-3-oxo-2-phenylpyrazolidine-1-carboxylate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 10h;	90%

: 3373-59-9
L-threonine methyl ester

: 1449786-45-1
(S)-4-amino-3-(2-(tert-butoxycarbonylamino)-4-phenylbutanamido)benzoic acid

: 1449786-48-4
(2S,3R)-methyl 2-(4-amino-3-((S)-2-(tert-butoxycarbonylamino)-4-phenylbutanamido) benzamido)-3-hydroxybutanoate

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere;	90%

: 3373-59-9
L-threonine methyl ester

: C14H13F6NO3

: C16H22N2O5

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran at 70℃; for 5h; Microwave irradiation;	90%

: 3373-59-9
L-threonine methyl ester

: 39739-45-2
methylpropioimidate hydrochloride

: (S)-2-Ethyl-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	89%

: 3373-59-9
L-threonine methyl ester

: 123-11-5
4-methoxy-benzaldehyde

: 936362-61-7
N-(p-methoxybenzyl)-L-threonine methyl ester

Conditions

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 0 - 20℃; for 17h;	89%

: 928150-63-4
N,N-diethyl(α,α-difluoro-4-methoxybenzyl)amine

: 3373-59-9
L-threonine methyl ester

: 704910-29-2
methyl (4S,5R)-2-(4-methoxyphenyl)-5-methyl-4,5-dihydrooxazole-4-carbonylate

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 1h;	89%

Methyl L-threoninate Specification

This chemical is called Methyl L-threoninate, and it can also be named as L-Threonine, methyl ester. With the molecular formula of C₅H₁₁NO₃, its molecular weight is 133.15. The CAS registry number of this chemical is 3373-59-9.

Other characteristics of the Methyl L-threoninate can be summarised as followings: (1)ACD/LogP: -1.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3; (4)ACD/LogD (pH 7.4): -1; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 4; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 72.55 Å²; (13)Index of Refraction: 1.461; (14)Molar Refractivity: 31.976 cm³; (15)Molar Volume: 116.488 cm³; (16)Polarizability: 12.676×10^-24cm³; (17)Surface Tension: 41.884 dyne/cm; (18)Density: 1.143 g/cm³; (19)Flash Point: 98.09 °C; (20)Enthalpy of Vaporization: 55.257 kJ/mol; (21)Boiling Point: 238.58 °C at 760 mmHg; (22)Vapour Pressure: 0.007 mmHg at 25°C.

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

Product Name

L-THREONINE METHYL ESTER

Synthetic route

Methyl L-threoninate Specification

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