- Boc-Thr(Bzl)-OH
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2026-07-09
- CAS:15260-10-3
- Min. Order: 1KG
- Purity: 98%min
- Supply Ability: 500kgs
- Boc-L-Thr(Bzl)-OH
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2026-07-09
- CAS:15260-10-3
- Min. Order: 1kg
- Purity: 98%
- Supply Ability: 1T+
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| | Boc-Thr(Bzl)-OH Basic information |
| | Boc-Thr(Bzl)-OH Chemical Properties |
| Melting point | 80-82 °C(lit.) | | Boiling point | 461.5±45.0 °C(Predicted) | | alpha | 22 º (c=2 in 95% ethanol) | | density | 1.152±0.06 g/cm3(Predicted) | | refractive index | 16.5 ° (C=1, MeOH) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | | pka | 3.50±0.10(Predicted) | | form | powder to crystal | | color | White to Almost white | | Optical Rotation | [α]20/D +16.5±1°, c = 1% in methanol | | BRN | 3065591 | | Major Application | peptide synthesis | | InChI | InChI=1S/C16H23NO5/c1-11(21-10-12-8-6-5-7-9-12)13(14(18)19)17-15(20)22-16(2,3)4/h5-9,11,13H,10H2,1-4H3,(H,17,20)(H,18,19)/t11-,13+/m1/s1 | | InChIKey | CTXPLTPDOISPTE-YPMHNXCESA-N | | SMILES | C(O)(=O)[C@H]([C@H](OCC1=CC=CC=C1)C)NC(OC(C)(C)C)=O | | CAS DataBase Reference | 15260-10-3(CAS DataBase Reference) | | EPA Substance Registry System | L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- (15260-10-3) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | TSCA | TSCA listed | | HS Code | 2924 29 70 | | Storage Class | 13 - Non Combustible Solids |
| | Boc-Thr(Bzl)-OH Usage And Synthesis |
| Chemical Properties | White crystalline | | Uses | Boc-O-benzyl-L-threonine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance. | | Application | Boc-Thr(Bzl)-OH is a standard building block for introduction of threonine amino-acid residues by Boc SPPS. | | reaction suitability | reaction type: Boc solid-phase peptide synthesis | | Synthesis | To a stirred solution of (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoic acid (250 g, 1.44 mol) in DMF (1 L) was added 60% sodium hydride (68 g, 2.85 mol) in batches at -20 °C and protected by nitrogen and stirring was continued for 2 hours. Subsequently, benzyl bromide (167 mL, 1.36 mol) was slowly added dropwise and the reaction mixture was continued to be stirred at room temperature for 3 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming complete consumption of the raw materials, the reaction was quenched with ice water and subsequently washed with ether (2 x 250 mL). The aqueous layer was separated and the pH was adjusted to about 2 with citric acid solution, followed by extraction with ethyl acetate (2 x 300 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford (2S,3R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid (320 g, 90% yield) as a thick paste.1H-NMR (500 MHz, DMSO-d6) data: δ 12.64 (broad single peak, 1H), 7.34-7.25 (multiple peaks, 5H), and 6.46 (double peak, J=8.5Hz, 1H), 4.53 (double peak, J=11.5Hz, 1H), 4.39 (double peak, J=12.0Hz, 1H), 4.00-3.98 (multiple peaks, 2H), 1.39 (single peak, 9H), 1.15 (double peak, J=6.0Hz, 3H). | | References | [1] Patent: WO2018/26763, 2018, A1. Location in patent: Page/Page column 63
[2] Patent: WO2014/120786, 2014, A1. Location in patent: Paragraph 0101
[3] Patent: WO2014/120783, 2014, A1. Location in patent: Paragraph 0093
[4] Patent: WO2017/195069, 2017, A1. Location in patent: Page/Page column 66
[5] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 5, p. 1369 - 1377 |
| | Boc-Thr(Bzl)-OH Preparation Products And Raw materials |
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