| Company Name: |
Alfa Aesar |
| Tel: |
400-6106006 |
| Email: |
saleschina@alfa-asia.com |
- Boc-L-Threonine
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2026-09-11
- CAS:2592-18-9
- Min. Order: 1KG
- Purity: 98%min
- Supply Ability: 500kgs
- Boc-L-Threonine
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- $10.00
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2026-03-20
- CAS:2592-18-9
- Min. Order: 1KG
- Purity: 99%
- Supply Ability: 10 mt
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| | Boc-L-Threonine Basic information |
| | Boc-L-Threonine Chemical Properties |
| 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. | | pka | 3.60±0.10(Predicted) | | form | powder to crystal | | color | White to Almost white | | Optical Rotation | [α]20/D 8.5±1°, c = 1% in acetic acid | | BRN | 2331474 | | Major Application | peptide synthesis | | 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) |
| | Boc-L-Threonine Usage And Synthesis |
| 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 |
| | Boc-L-Threonine Preparation Products And Raw materials |
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