| Identification | Back Directory | [Name]
Methyl N-(tert-butoxycarbonyl)-L-threoninate | [CAS]
79479-07-5 | [Synonyms]
79479-07-5
Boc-L-Thr-OMe
(Tert-Butoxy)Carbonyl Thr-OMe
N-BOC-L-threonine methylester
N-Boc-L-threonine methyl ester, 97.5%
Boc-L-threonine methyl ester≥ 98% (HPLC)
N-(TERT-BUTOXYCARBONYL)-L-THREONINE MET&
Methyl N-(tert-butoxycarbonyl)-L-threoninate
Methyl N-(tert-butoxycarbonyl)-L-threoninate USP/EP/BP
L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester
(2S,3R)-methyl 2-(tert-butoxycarbonylamino)-3-hydroxybutanoate
methyl (2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanoate
(2S, 3S)-2-Tert-butoxycarbonylaMino-3-hydroxy-butyric acid Methyl ester Boc-Thr-OMe | [Molecular Formula]
C10H19NO5 | [MDL Number]
MFCD00270479 | [MOL File]
79479-07-5.mol | [Molecular Weight]
233.262 |
| Chemical Properties | Back Directory | [Boiling point ]
206 °C(lit.) | [density ]
1.123±0.06 g/cm3(Predicted) | [refractive index ]
n20/D 1.45(lit.) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform (Sparingly), Dichloromethane (Sparingly), DMF (Sparingly) | [form ]
Viscous Liquid | [pka]
11.00±0.46(Predicted) | [color ]
Yellow | [Water Solubility ]
Slightly soluble in water. | [Major Application]
peptide synthesis | [InChI]
1S/C10H19NO5/c1-6(12)7(8(13)15-5)11-9(14)16-10(2,3)4/h6-7,12H,1-5H3,(H,11,14)/t6-,7+/m1/s1 | [InChIKey]
MZMWAPNVRMDIPS-RQJHMYQMSA-N | [SMILES]
COC(=O)[C@@H](NC(=O)OC(C)(C)C)[C@@H](C)O |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow transparent oil | [Uses]
N-Boc-L-threonine methyl ester is used as pharmaceutical intermediates and chemical intermediate. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of Boc-D-alanine methyl ester from (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoic acid and dimethyl sulfate was as follows:
1) Synthesis of N-Boc-L-threonine methyl ester: Potassium carbonate (34.7 g, 250 mmol) and dimethyl sulfate (29.3 g, 232 mmol) were sequentially added to a solution of N-Boc-L-threonine (50.0 g, 213 mmol) in acetone (250 mL). The reaction mixture was heated to reflux for 1 h and subsequently cooled to room temperature in air. Insoluble solids were removed by filtration and the filtrate was concentrated under reduced pressure to remove the solvent to afford N-tert-butoxycarbonyl-L-threonine methyl ester as a colorless oil (54.6 g, 100% yield). The product was characterized by 1H-NMR (300 MHz, DMSO-d6): δ 1.26 (3H, d, J = 6.42 Hz), 1.46 (9H, s), 2.02 (1H, d, J = 5.14 Hz), 3.78 (3H, s), 4.28 (1H, m), 5.29 (1H, m). Mass spectra (FAB) showed molecular ion peak m/z: 234 ([M + H]+). | [References]
[1] Patent: EP1621537, 2006, A1. Location in patent: Page/Page column 25
[2] Patent: CN108003048, 2018, A. Location in patent: Paragraph 0013 |
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J & K SCIENTIFIC LTD.
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Alfa Aesar
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Energy Chemical
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Sigma-Aldrich
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Shanghai GL Peptide Ltd.
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