| Identification | More | [Name]
Boc-L-Threonine | [CAS]
2592-18-9 | [Synonyms]
BOC-L-THREONINE
BOC-L-THREONINE-OH
BOC-L-THR-OH
BOC-THREONINE
BOC-THR-OH
N-ALPHA-T-BOC-L-THREONINE
N-ALPHA-T-BUTOXYCARBONYL-L-THREONINE
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-THREONINE
N-BOC-L-THREONINE
N-T-BUTOXYCARBONYL-L-THREONINE
N-(TERT-BUTOXYCARBONYL)-L-THREONINE
N-(TERT-BUTOXYCARBONYL)-P-THREONINE
N-TERT-BUTYLOXYCARBONYL-L-THREONINE
N-(TERT-BUTOXYCARBONYL)-L-THREONINE 98%
N-T-BOC-L-THREONINE CRYSTALLINE
Boc-L-Threionine
N-ALPHA-T-BUTYLOXYCARBONYL-L-THREONINE
N-Boc-L-threonine, 98+%
BOC-L-THREONINE extrapure
N-(tert-Butoxycarbonyl)-L-threonine, Boc-L-threonine | [EINECS(EC#)]
219-987-6 | [Molecular Formula]
C9H17NO5 | [MDL Number]
MFCD00065946 | [Molecular Weight]
219.23 | [MOL File]
2592-18-9.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE AMORPHOUS POWDER | [Melting point ]
80-82 °C(lit.) | [alpha ]
-8.5 º (c=1, acetic acid) | [Boiling point ]
360.05°C (rough estimate) | [density ]
1.2470 (rough estimate) | [refractive index ]
-7 ° (C=1, AcOH) | [storage temp. ]
−20°C
| [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
powder to crystal | [pka]
3.60±0.10(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]20/D 8.5±1°, c = 1% in acetic acid | [BRN ]
2331474 | [InChI]
InChI=1S/C9H17NO5/c1-5(11)6(7(12)13)10-8(14)15-9(2,3)4/h5-6,11H,1-4H3,(H,10,14)(H,12,13)/t5-,6+/m1/s1 | [InChIKey]
LLHOYOCAAURYRL-RITPCOANSA-N | [SMILES]
C(O)(=O)[C@H]([C@H](O)C)NC(OC(C)(C)C)=O | [CAS DataBase Reference]
2592-18-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29241990 |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE AMORPHOUS POWDER | [Uses]
N-Boc-L-threonine is an N-Boc-protected form of L-Threonine (T405500). L-Threonine is an essential amino acid that is commonly used as a feed and food additive. L-Threonine is produced in mass quantities by mutant Escherichia coli strains for research and food nutrition purposes. L-Threonine can be naturally found in fish and poultry, and is incorporated in some important proteins in the human body (such as hemoglobin and insulin). | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutyric acid from L-threonine and di-tert-butyl dicarbonate was as follows:
1. To a methanol (5 mL) solution of L-threonine (400 mg, 3.36 mmol), a water (5 mL) solution of sodium bicarbonate (434 mg, 5.17 mmol) was added, followed by di-tert-butyl dicarbonate (1.07 g, 4.90 mmol).
2. The reaction mixture was stirred at room temperature for 3 days.
3. Upon completion of the reaction, the solvent was removed by vacuum distillation. 4.
4. The residue was diluted with water (20 mL) and washed with ether (2 x 20 mL).
5. The aqueous layer was acidified with saturated aqueous sodium bisulfite and then extracted with 2-methyltetrahydrofuran.
6. The organic layer was dried over anhydrous sodium sulfate and subsequently concentrated in vacuo to afford the title compound (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutyric acid as a white solid (730 mg, 99% yield).
7. The product was characterized by 1H NMR (400 MHz, CDCl3) and LC-MS: 1H NMR δ 1.24 (d, 3H), 1.44 (s, 9H), 4.26 (d, 1H), 4.40 (d, 1H), 5.52 (d, 1H), 5.69 (br s, 1H); LCMS Rt = 1.68 min, MS m/z 218 [M + H]+. | [References]
[1] Patent: WO2013/114250, 2013, A1. Location in patent: Page/Page column 161; 162
[2] Patent: WO2013/110643, 2013, A1. Location in patent: Paragraph 00118; 00119
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1795 - 1802
[4] Patent: CN102993200, 2016, B. Location in patent: Paragraph 0043; 0044; 0045
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5770 - 5781 |
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