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| | N-Carbobenzyloxy-L-threonine methyl ester Basic information |
| Product Name: | N-Carbobenzyloxy-L-threonine methyl ester | | Synonyms: | N-CARBOBENZOXY-L-THREONINE METHYL ESTER;N-CARBOBENZYLOXY-L-THREONINE METHYL ESTER;N-ALPHA-CARBOBENZOXY-L-THREONINE METHYL ESTER;Z-L-THREONINE METHYL ESTER;Z-THREONINE-OME;L-Threonine, N-(phenylmethoxy)carbonyl-, methyl ester;CBZ-L-THREONINE METHYL ESTER;N-Carbobenzyloxy-L-threonine methyl ester, Z-L-Threonine methyl ester | | CAS: | 57224-63-2 | | MF: | C13H17NO5 | | MW: | 267.28 | | EINECS: | | | Product Categories: | ADVANCED INT. | | Mol File: | 57224-63-2.mol |  |
| | N-Carbobenzyloxy-L-threonine methyl ester Chemical Properties |
| Melting point | 92-94 °C(lit.) | | alpha | -18 º (c=1, MeOH) | | Boiling point | 410.46°C (rough estimate) | | density | 1.2100 (rough estimate) | | refractive index | 1.4365 | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | form | Powder | | pka | 10.79±0.46(Predicted) | | color | White | | Optical Rotation | [α]25/D 18°, c = 1 in methanol | | Water Solubility | miscible | | BRN | 2220800 | | Major Application | peptide synthesis | | InChI | 1S/C13H17NO5/c1-9(15)11(12(16)18-2)14-13(17)19-8-10-6-4-3-5-7-10/h3-7,9,11,15H,8H2,1-2H3,(H,14,17)/t9-,11+/m1/s1 | | InChIKey | OPZWAOJFQFYYIX-KOLCDFICSA-N | | SMILES | COC(=O)[C@@H](NC(=O)OCc1ccccc1)[C@@H](C)O | | CAS DataBase Reference | 57224-63-2(CAS DataBase Reference) |
| Safety Statements | 24/25 | | WGK Germany | 3 | | Storage Class | 11 - Combustible Solids |
| | N-Carbobenzyloxy-L-threonine methyl ester Usage And Synthesis |
| Chemical Properties | white to off-white powder | | Uses | peptide synthesis | | reaction suitability | reaction type: solution phase peptide synthesis | | Synthesis | In a 2L beaker, 100 g of L-threonine methyl ester hydrochloride was dissolved in 600 ml of water and the pH was adjusted to a suitable range using sodium bicarbonate. Subsequently, 110 g of benzyl chloroformate (Z-Cl) was slowly added dropwise and the pH of the reaction system was kept between 8-9, which was adjusted using 2 M sodium hydroxide solution. After completion of the reaction, 1 L of ethyl acetate was added for extraction. The organic phase was washed sequentially with 500 ml of water and 500 ml of saturated saline, and then dried with 100 g of anhydrous sodium sulfate. After filtration, it was concentrated to dryness under reduced pressure to obtain a solid product. The solid was dissolved in 600 ml of a suitable solvent for crystallization, filtered and dried to give 140 g of N-benzyloxycarbonyl-L-threonine methyl ester (Z-Thr-OMe) in 89.1% yield. | | References | [1] Patent: CN106631900, 2017, A. Location in patent: Paragraph 0015
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 24, p. 3697 - 3703
[3] Justus Liebigs Annalen der Chemie, 1962, vol. 656, p. 190 - 204
[4] Journal of Organic Chemistry, 1985, vol. 50, # 23, p. 4515 - 4523
[5] Patent: WO2010/17060, 2010, A1. Location in patent: Page/Page column 44-45 |
| | N-Carbobenzyloxy-L-threonine methyl ester Preparation Products And Raw materials |
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