Boc-O-benzyl-L-threonine

Base Information

• Chemical Name: Boc-O-benzyl-L-threonine
• CAS No.: 15260-10-3
• Deprecated CAS: 111516-03-1,172846-16-1,54784-63-3,1416064-93-1,1422430-41-8,1453873-39-6
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362
• Hs Code.: 2924 29 70
• European Community (EC) Number: 239-304-5
• DSSTox Substance ID: DTXSID20884829
• Nikkaji Number: J218.388I
• Wikidata: Q76139869
• Mol file: 15260-10-3.mol

Synonyms:Boc-Thr(Bzl)-OH;15260-10-3;Boc-O-benzyl-L-threonine;N-(tert-Butoxycarbonyl)-O-benzyl-L-threonine;N-Boc-O-benzyl-L-threonine;O-Benzyl-N-tert-butoxycarbonyl-L-threonine;(2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoic acid;EINECS 239-304-5;NSC 334365;N-((1,1-Dimethylethoxy)carbonyl)-O-(phenylmethyl)-L-threonine;(2S,3R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid;L-Threonine, N-((1,1-dimethylethoxy)carbonyl)-O-(phenylmethyl)-;L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-;(2S,3R)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}butanoic acid;MFCD00066062;N-[(1,1-Dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-threonine;Boc-L-Thr(OBn)-OH;O-benzyl-N-(tert-butoxycarbonyl)-L-threonine;SCHEMBL400187;DTXSID20884829;AKOS015889684;AKOS015924178;AC-8633;CS-W004110;HY-W004110;t-butyloxycarbonyl-O-benzyl-L-threonine;AS-12101;Boc-Thr(Bzl)-OH, >=99.0% (T);AM20030040;B1630;Nalpha-t-butoxycarbonyl-O-benzyl-L-threonine;o-Benzyl-N-(tert-butoxycarbonyl)threonine #;I10416;M03326;nalpha-tert-butoxycarbonyl-o-benzyl-l-threonine;EN300-3406416;N-alpha-t-Butyloxycarbonyl-O-benzyl-L-threonine;Nalpha-(tert-butoxycarbonyl)-O-benzyl-L-threonine;Q-101843;(2S,3R)-3-benzyloxy-2-tertbutoxycarbonylaminobutyric acid;(2S,3R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoicacid;(2S,3R)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)butanoic acid;(2S,3R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino) butanoic acid;Butyric acid, 3-(benzyloxy)-2-(carboxyamino)-, N-tert-butyl ester,Ls-threo-

Chemical Property of Boc-O-benzyl-L-threonine

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 1.36E-07mmHg at 25°C
• Melting Point: 80-82 °C(lit.)
• Refractive Index: 16.5 ° (C=1, MeOH)
• Boiling Point: 461.5 °C at 760 mmHg
• PKA: 3.50±0.10(Predicted)
• Flash Point: 232.9 °C
• PSA: 84.86000
• Density: 1.152 g/cm³
• LogP: 2.96050
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 371

Purity/Quality:

99% ^*data from raw suppliers

Boc-O-benzyl-L-threonine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)O)NC(=O)OC(C)(C)C)OCC1=CC=CC=C1
• Isomeric SMILES: C[C@H]([C@@H](C(=O)O)NC(=O)OC(C)(C)C)OCC1=CC=CC=C1
• 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.

Technology Process of Boc-O-benzyl-L-threonine

There total 8 articles about Boc-O-benzyl-L-threonine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

→ N-Boc-O-benzyl-L-threonine (15260-10-3)

Guidance literature:

With trimethyltin(IV) hydroxide; In 1,2-dichloro-ethane; for 9h; Heating;

DOI:10.1016/S0040-4020(98)00805-9

Reference yield: 90.0%

Boc-Thr-OH (2592-18-9) + benzyl bromide (100-39-0) → N-Boc-O-benzyl-L-threonine (15260-10-3)

Guidance literature:

Boc-Thr-OH; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at -20 ℃; for 2h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 - 25 ℃; for 3h;

Reference yield: 83.0%

(2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester (185461-75-0) → N-Boc-O-benzyl-L-threonine (15260-10-3)

Guidance literature:

With magnesium bromide; In dichloromethane; for 3h; Ambient temperature; addition at -20 deg C, 0.5 h;

DOI:10.1016/S0040-4039(97)00863-0

upstream raw materials:

O-benzyl-L-threonine

1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate

Boc-Thr-OH

benzyl bromide

Downstream raw materials:

(2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid 2-cyano-ethyl ester

N^α-(t-butoxycarbonyl)-O-(benzyl)threonylalanine benzyl ester

Boc-Thr(Bn)-Leu-OBn

{(1S,2R)-2-Benzyloxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propyl}-carbamic acid tert-butyl ester

Refernces

• 1、 Rodin,Baygildiev,Krylov,Osipov,Krylov,Yashkir,Rybalchenko. "Synthesis of the Tripeptides Tyr-Thr-Lys Phosphorylated with Isopropyl Methyl- and (Deuteromethyl)phosphonochloridates as Reference Standards for the Analysis of Biomedical Samples". . p. 2103 - 2107. Retrieved 2019/11/29.
• 2、 -. "OXABOROLE ESTERS AND USES THEREOF". Page/Page column 66. . Retrieved 2017/12/05.