O-Benzyl-L-threonine

Base Information

• Chemical Name: O-Benzyl-L-threonine
• CAS No.: 4378-10-3
• Molecular Formula: C11H15NO3
• Molecular Weight: 209.245
• DSSTox Substance ID: DTXSID80426224
• Nikkaji Number: J265.521G
• Wikidata: Q27467869
• Mol file: 4378-10-3.mol

Synonyms:4378-10-3;H-Thr(Bzl)-OH;O-BENZYL-L-THREONINE;(2S,3R)-2-Amino-3-(benzyloxy)butanoic acid;L-Threonine, O-(phenylmethyl)-;H-L-Thr(bzl)-oh;(2S,3R)-2-amino-3-phenylmethoxybutanoic acid;O-benzyl-threonine;L-Threonine benzyl ester;(2S,3R)-2-azaniumyl-3-phenylmethoxybutanoate;Thr(Bzl);SCHEMBL288386;DTXSID80426224;ONOURAAVVKGJNM-SCZZXKLOSA-N;MFCD00037768;AKOS016003047;AM82264;CS-W015160;HY-W014444;AS-56514;O-BenZyl-L-threonine (H-L-Thr(BZl)-OH);(2S,3R)-2-amino-3-benzyloxy-butyric acid;D94987;EN300-258158;Q27467869

Chemical Property of O-Benzyl-L-threonine

Chemical Property:

• Melting Point: 197 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 362.9±37.0 °C(Predicted)
• PKA: 2.13±0.10(Predicted)
• PSA: 72.55000
• Density: 1.180±0.06 g/cm3(Predicted)
• LogP: 1.70390
• Storage Temp.: Store at RT.
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 209.10519334
• Heavy Atom Count: 15
• Complexity: 202

Purity/Quality:

98%min ^*data from raw suppliers

H-Thr(Bzl)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of O-Benzyl-L-threonine

There total 12 articles about 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: 100.0%

Z(OMe)-Thr(Bzl)-OH → O-benzyl-L-threonine (4378-10-3)

Guidance literature:

With methanesulfonic acid; 3-methyl-phenol; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1248/cpb.41.954

Reference yield: 95.0%

isoamyl Boc-L-Thr(Bzl) → O-benzyl-L-threonine (4378-10-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/c6ob01189f

Reference yield: 93.0%

N-benzyloxycarbonyl-O-benzyl-L-threonine (69863-36-1) → O-benzyl-L-threonine (4378-10-3)

Guidance literature:

With ammonia; hydrogen; palladium on activated charcoal; In methanol; for 20h; Ambient temperature;

DOI:10.1016/0040-4039(95)00527-J

upstream raw materials:

N-benzyloxycarbonyl-O-benzyl-L-threonine

O-benzyl 2,2,2-trichloroacetimidate

Threonine mono sodium salt

benzyl bromide

Downstream raw materials:

4-(1-benzyloxy-ethyl)-oxazolidine-2,5-dione

(2S,3R)-Fmoc-O-benzyl-threonine

rac-allo-threonine

N-(phenoxycarbonyl)-O-benzyl-L-threonine

Refernces

• 1、 Stuhr-Hansen, Nicolai,Padrah, Shahrokh,Str?mgaard, Kristian. "Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids". supporting information. p. 4149 - 4151. Retrieved 2015/02/02.
• 2、 Wang, Jidong,Okada, Yoshio,Li, Wei,Yokoi, Toshio,Zhu, Jintao. "2,2-Difluoro-1,3,2-oxazaborolidin-5-ones: Novel approach for selective side-chain protection of serine and threonine". . p. 621 - 624. Retrieved 2007/10/03.