O-tert-Butyl-L-threonine tert-butyl ester supplier

Name
H-THR(TBU)-OTBU
EINECS
CAS No. 5854-78-4
Article Data12
CAS DataBase
Density 0.959 g/cm³
Solubility
Melting Point 74-75 °C
Formula C₁₂H₂₅NO₃
Boiling Point 296.1 °C at 760 mmHg
Molecular Weight 231.335
Flash Point 79.3 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Butyricacid, 2-amino-3-tert-butoxy-, tert-butyl ester (7CI);Butyric acid,2-amino-3-tert-butoxy-, tert-butyl ester, L- (8CI);O-tert-Butyl-L-threoninetert-butyl ester;O-tert-Butylthreonine tert-butyl ester;
PSA 61.55000
LogP 2.55930

Synthetic route

: 72-19-5
L-threonine

: 115-11-7
isobutene

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

Conditions

Conditions	Yield
Stage #1: L-threonine With trifluorormethanesulfonic acid In 1,2-dimethoxyethane at -10 - 5℃; Stage #2: isobutene In 1,2-dimethoxyethane at -15 - -10℃; for 48h; Reagent/catalyst; Solvent;	67.2%
Stage #1: L-threonine; isobutene With sulfuric acid In 1,2-dimethoxyethane at -5 - 5℃; for 24h; Stage #2: With ammonia In water at 0℃;

: 72-19-5
L-threonine

: 1634-04-4
tert-butyl methyl ether

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

Conditions

Conditions	Yield
With sulfuric acid at 25℃; for 2h; Molecular sieve; chemoselective reaction;	30%

: 14437-51-5
N-Carbobenzoxy-O-tert.-butyl-L-threonin-tert.-butylester

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

Conditions

Conditions	Yield
With hydrogen; palladium In methanol
With hydrogen; palladium on activated charcoal In methanol
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide
With hydrogen; palladium on activated charcoal In methanol for 2h; Ambient temperature;

: 19728-63-3
N-benzyloxycarbonyl-L-treonine

: 115-11-7
isobutene

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

Conditions

Conditions	Yield
(i) H2SO4, CH2Cl2, (ii) H2, Pd-BaSO4, MeOH; Multistep reaction;
(i) H2SO4, (ii) (hydrogenolysis); Multistep reaction;
(i) H2SO4, CH2Cl2, (ii) H2, Pd-C, EtOH; Multistep reaction;

: 1634-04-4
tert-butyl methyl ether

: 17083-30-6, 66748-90-1, 67580-85-2, 150693-46-2, 150693-47-3
tert-butyl (2S,3R)-2-amino-3-hydroxybutanoate

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

Conditions

Conditions	Yield
With ZSM-5 supported silicotungstic acid at 70℃; Temperature;

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 158000-10-3
2-Azidoethyl α-D-galactopyranosiduronic acid

: N-(2-Azidoethyl α-D-galactopyranosiduronoyl)-O-(tert-butyl)-L-threonine tert-butyl ester

Conditions

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 20℃; for 72h;	100%

: 1147133-24-1
C12H15NO7

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 1147134-79-9
C24H38N2O9

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 24h;	100%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 35661-40-6
N-Fmoc L-Phe

: 87720-56-7
t-butyl-N-fluoren-9-ylmethyloxycarbonyl-L-phenylalanyl-O-t-butyl-L-threonine

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 18h;	99%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 129765-95-3
3-[(tert-butoxycarbonyl)amino]-3-methylbutanoic acid

: Boc-β-HoAib-L-Thr(t-Bu)-O-t-Bu

Conditions

Conditions	Yield
With pentamethoxy tantalum; 1-(Trimethylsilyl)imidazole In neat (no solvent) at 50℃; for 48h; Inert atmosphere; Sealed tube;	99%

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

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: Boc-L-Ala-L-Thr(t-Bu)-O-t-Bu

Conditions

Conditions	Yield
With pentamethoxy tantalum; 1-(Trimethylsilyl)imidazole In neat (no solvent) at 50℃; for 72h; Inert atmosphere; Sealed tube;	98%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 127879-03-2
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-2-(2-Acryloylamino-ethoxy)-3,5-dihydroxy-6-methyl-tetrahydro-pyran-4-yloxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

: 136632-51-4
(2S,3R)-2-({(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-2-(2-Acryloylamino-ethoxy)-3,5-dihydroxy-6-methyl-tetrahydro-pyran-4-yloxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carbonyl}-amino)-3-tert-butoxy-butyric acid tert-butyl ester

Conditions

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 20℃;	95%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 557095-50-8
2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-thiobutyric acid S-(2-formyl-4-nitro-phenyl) ester

: 557095-67-7
Fmoc-Val-Thr(t-Bu)-O-Bu-t

Conditions

Conditions	Yield
With N-methylmaleimide; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; water; N,N-dimethyl-formamide at 20℃; for 2.5h;	95%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 136632-48-9
2-azidoethyl 3-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosiduronic acid

: (2S,3R)-2-{[(2S,3S,4S,5R,6R)-6-(2-Azido-ethoxy)-3,5-dihydroxy-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carbonyl]-amino}-3-tert-butoxy-butyric acid tert-butyl ester

Conditions

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 20℃;	92%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: (2E,4E)-dodeca-2,4-dien-11-ynoic acid

: tert-butyl O-(tert-butyl)-N-((2E,4E)-dodeca-2,4-dien-11-ynoyl)-L-threoninate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere;	90%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 39178-35-3
isonicotinoyl chloride hydrochloride

: C18H28N2O4

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2.25h;	88.6%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: N-(2-nitrobenzenesulfonyl)-O-t-butyl-L-threonine t-butyl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; Acylation;	88%

: 2483-51-4
N-[(benzyloxy)carbonyl]-L-alanyl-L-alanine methyl ester

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: C26H41N3O7

Conditions

Conditions	Yield
With 2,2':6',2'':6'',2'''-quaterpyridine; pentamethoxy tantalum at 70℃; for 48h;	84%

: 2389-60-8
Z-Lys(Boc)-OH

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 52616-65-6
Nα-Z-Nε-BOC-L-lysyl-O-tert-butyl-L-threonine tert-butyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 1h; then 3 h at 20 deg C;	82%

: (2E,4E)-11-methyldodeca-2,4-dienoic acid

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: tert-butyl O-(tert-butyl)-N-((2E,4E)-11-methyldodeca-2,4-dienoyl)-L-threoninate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	81%

: 23574-01-8
3-benzylamino-propionic acid methyl ester

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: C22H36N2O4

Conditions

Conditions	Yield
With pentamethoxy tantalum at 60℃; for 48h;	75%

: 5681-98-1
Isotridecanoic Acid

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: tert-butyl O-(tert-butyl)-N-(11-methyldodecanoyl)-L-threoninate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	75%

: 28875-17-4
(S)-N-(tert-butoxycarbonyl)alanine methyl ester

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: Boc-L-Ala-L-Thr(t-Bu)-O-t-Bu

Conditions

Conditions	Yield
With pentamethoxy tantalum In neat (no solvent) at 60℃; for 72h; Inert atmosphere; Sealed tube;	71%

: 858104-55-9
(3R,4R)-1-(4-fluorophenyl)-3-[(4-fluorobenzoyl)methylthio]-4-{4-[N-(carboxymethyl)carbamoylmethoxy]phenyl}azetidin-2-one

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycyl-L-threonine

Conditions

Conditions	Yield
Stage #1: (3R,4R)-1-(4-fluorophenyl)-3-[(4-fluorobenzoyl)methylthio]-4-{4-[N-(carboxymethyl)carbamoylmethoxy]phenyl}azetidin-2-one; (2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate With 4-methyl-morpholine In dichloromethane at 20℃; Stage #2: With (1,1,1-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate In dichloromethane Stage #3: With trifluoroacetic acid In dichloromethane for 2h;	63%

Yield

Stage #1: (3R,4R)-1-(4-fluorophenyl)-3-[(4-fluorobenzoyl)methylthio]-4-{4-[N-(carboxymethyl)carbamoylmethoxy]phenyl}azetidin-2-one; (2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate With 4-methyl-morpholine In dichloromethane at 20℃;
Stage #2: With (1,1,1-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate In dichloromethane
Stage #3: With trifluoroacetic acid In dichloromethane for 2h;

63%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: tert-butyl (S)-(1-((2,2-dicyanoethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

: tert-butyl N-(tert-butoxycarbonyl)-L-phenylalanylglycyl-O-(tert-butyl)-L-threoninate

Conditions

Conditions	Yield
With oxygen; cesium acetate In water; N,N-dimethyl-formamide at 20℃; for 17h; Inert atmosphere;	51%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 107-18-6
allyl alcohol

: (2S, 3R)-tert-butyl 3-(tert-butoxy)-2-((3-hydroxypropyl)amino)butanoate

Conditions

Conditions	Yield
With potassium phosphate; [(bis(2-dicyclohexylphosphinoethyl)amine)Fe(CO)Br2]; sodium triethylborohydride In cyclohexane at 80℃; for 24h; Inert atmosphere; Sealed tube;	42%

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 68800-26-0
N-tert-butoxycarbonylglycylglycylphenylalanylmethionine

: Boc-Gly-Gly-Phe-Met-Thr(tBu)-OtBu

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 30 min, -20 deg C; 2.) 0 deg C, 2 h; 3.) r.t., 18 h;	36.1%

: 3256-57-3
N-benzyloxycarbonyl-L-asparagine p-nitrophenyl ester

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 2596-12-5
N-Benzyloxycarbonyl-L-asparaginyl-O-tert.-butyl-L-threonin-tert.-butylester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 72-19-5
L-threonine

Conditions

Conditions	Yield
With trifluoroacetic acid

: 75-77-4
chloro-trimethyl-silane

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: N-(Trimethylsilyl)-O-tert-butylthreonin-tert-butylester

Conditions

Conditions	Yield
With triethylamine In dichloromethane

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 86060-87-9
Fmoc-Val-OPfp

: 557095-67-7
Fmoc-Val-Thr(t-Bu)-O-Bu-t

: 5854-78-4
(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate

: 5891-41-8
Nα-benzyloxycarbonyl-glycyl-prolyl-alanine

: 79141-72-3
Nα-benzyloxycarbonyl-glycyl-prolyl-alanyl-O-tert-butyl-threonine tert-butyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide 1.) DMF/CH2Cl2, 0 deg C, 20 min, 2.) room temp., 12 h; Yield given. Multistep reaction;

O-tert-Butyl-L-threonine tert-butyl ester Specification

This chemical is called tert-Butyl O-tert-butyl-L-threoninate, and its CAS registry number is 5854-78-4. With the molecular formula of C₁₂H₂₅NO₃, its molecular weight is 231.33. Additionally, this chemical should be sealed at the temperature of -15°C.

Other characteristics of the tert-Butyl O-tert-butyl-L-threoninate can be summarised as followings: (1)ACD/LogP: 2.64; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.92; (4)ACD/LogD (pH 7.4): 2.62; (5)ACD/BCF (pH 5.5): 11.36; (6)ACD/BCF (pH 7.4): 57.12; (7)ACD/KOC (pH 5.5): 123.31; (8)ACD/KOC (pH 7.4): 620.3; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 38.77 Å²; (13)Index of Refraction: 1.448; (14)Molar Refractivity: 64.54 cm³; (15)Molar Volume: 240.9 cm³; (16)Polarizability: 25.58×10^-24cm³; (17)Surface Tension: 30.8 dyne/cm; (18)Density: 0.959 g/cm³; (19)Flash Point: 79.3 °C; (20)Enthalpy of Vaporization: 53.59 kJ/mol; (21)Boiling Point: 296.1 °C at 760 mmHg; (22)Vapour Pressure: 0.00146 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(OC(C)(C)C)[C@@H](N)[C@H](OC(C)(C)C)C
2.InChI: InChI=1/C12H25NO3/c1-8(15-11(2,3)4)9(13)10(14)16-12(5,6)7/h8-9H,13H2,1-7H3/t8-,9+/m1/s1
3.InChIKey: PPDIUNOGUIAFLV-BDAKNGLRBA

Product Name

H-THR(TBU)-OTBU

Synthetic route

O-tert-Butyl-L-threonine tert-butyl ester Specification

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