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Fmoc-o-tert-butyl-l-threonine

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Name

Fmoc-o-tert-butyl-l-threonine

EINECS 276-261-1
CAS No. 71989-35-0 Density 1.197 g/cm3
PSA 84.86000 LogP 4.57280
Solubility N/A Melting Point 131-134 °C
Formula C23H27NO5 Boiling Point 581.7 °C at 760 mmHg
Molecular Weight 397.471 Flash Point 305.6 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety 24/25-36/37/39-27-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 71989-35-0 (Fmoc-O-tert-Butyl-L-threonine) Hazard Symbols IrritantXi
Synonyms

(2S,3R)-2-(((9-Fluorenylmethoxy)carbonyl)amino)-3-(tert-butoxy)butanoicacid;(2S,3R)-3-tert-Butoxy-2-[[[[9H-fluoren-9-yl]methoxy]carbonyl]amino)butanoicacid;N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylthreonine;Fmoc-Thr(tBu)-OH;L-Threonine,O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;

Article Data 14

Fmoc-o-tert-butyl-l-threonine Synthetic route

4378-13-6

(O-tert-butyl)-L-threonine

102774-86-7

9-fluorenylmethyl N-succinimidyl carbonate

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
With triethylamine In water; acetonitrile for 1h;70%

(2S,3R)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
With magnesium bromide In dichloromethane for 3h; Ambient temperature; addition at -20 deg C, 0.5 h;67%
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

132776-34-2

O-tert-Butyl-L-threonine Methyl Ester p-Toluenesulfonate

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
With sodium hydroxide 1.) H2O, 0 deg C, 2 h; 2.) p-dioxane, 0 deg C to r.t., 24 h; Yield given. Multistep reaction;
146346-73-8

Fmoc-Thr(but)-O-Pha

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
With acetic acid; zinc Yield given;
275827-11-7

N-(9-Fluorenylmethoxycarbonyl)-O-(tert-butyl)-L-threonin-(2-phenyl-2-trimethylsilyl)ethylester

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dichloromethane at 20℃; β-fragmentation;
73731-37-0

Fmoc-Thr-OH

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diisopropylethylamine / ethyl acetate
2: 240 h
3: zinc, acetic acid
View Scheme
125760-27-2

N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 240 h
2: zinc, acetic acid
View Scheme
28920-43-6

(fluorenylmethoxy)carbonyl chloride

1254943-38-8

C8H17NO3*ClH

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;
67-56-1

methanol

72-19-5

L-threonine

82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

115-11-7

isobutene

71989-35-0

Fmoc-Thr(tBu)-OH

Conditions
ConditionsYield
Stage #1: methanol; L-threonine With thionyl chloride at 40 - 45℃; for 20h;
Stage #2: isobutene With sulfuric acid In dichloromethane at 0 - 5℃;
Stage #3: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide Further stages;

C29H30N4O5

A

71989-35-0

Fmoc-Thr(tBu)-OH

B

2592-95-2

benzotriazol-1-ol

Conditions
ConditionsYield
With water for 24h; Kinetics;

Fmoc-o-tert-butyl-l-threonine Chemical Properties

The Molecular Structure of Fmoc-o-tert-butyl-l-threonine (CAS NO.71989-35-0):

Molecular Formula: C23H27NO5
Molecular Weight: 397.46 
Nominal Mass: 397 Da
Average Mass: 397.4642 Da
Monoisotopic Mass: 397.188923 Da 
Index of Refraction: 1.568
Molar Refractivity: 108.74 cm3
Molar Volume: 332 cm3
Surface Tension: 47.8 dyne/cm
Density: 1.197 g/cm3
Flash Point: 305.6 °C
Enthalpy of Vaporization: 91.5 kJ/mol
Boiling Point: 581.7 °C at 760 mmHg 
Melting point: 131-134 °C
Vapour Pressure: 2.24E-14 mmHg at 25°C 
Storage temp: 2-8°C 
Soluble in ethyl acetate, insoluble in petroleum ether
InChI
InChI=1/C23H27NO5/c1-14(29-23(2,3)4)20(21(25)26)24-22(27)28-13-19-17-11-7-5-9-15(17)16-10-6-8-12-18(16)19/h5-12,14,19-20H,13H2,1-4H3,(H,24,27)(H,25,26)
Smiles
C[C@@H](OC(C)(C)C)[C@@H](NC(=O)OCC1c2c(cccc2)c2c1cccc2)C(O)=O 
Appearance: white to light yellow crystal powder
IUPAC: 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]butanoic acid    
Product Categories: Fluorenes, Flurenones;Amino Acid Derivatives;Amino Acids;Threonine [Thr, T];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series 

Fmoc-o-tert-butyl-l-threonine Uses

 Fmoc-o-tert-butyl-l-threonine (CAS NO.71989-35-0) can be used for peptide synthesis and protected amino acid monomer.

Fmoc-o-tert-butyl-l-threonine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 24/25-36/37/39-27-26 
S24/25: Avoid contact with skin and eyes
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S27: Take off immediately all contaminated clothing
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany: 3

Fmoc-o-tert-butyl-l-threonine Specification

 Fmoc-o-tert-butyl-l-threonine (CAS NO.71989-35-0) is also called as 9-Fluorenylmethoxycarbonyl-o-t-butyl-l-theonine ; 9-Fluorenylmethoxycarbonyl-o-t-butyl-l-threonine ; Fmoc-o-t-butyl-l-threonine ; Fmoc-l-thr(o-t-butyl) ; Fmoc-l-threonine(o-t-butyl) ; Fmoc-l-threonine (tbu) ; Fmoc-l-threonine t-butyl ether .

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