Boc-O-benzyl-D-threonine

Base Information

• Chemical Name: Boc-O-benzyl-D-threonine
• CAS No.: 69355-99-3
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362
• Hs Code.: 2924 29 70
• European Community (EC) Number: 858-015-0
• DSSTox Substance ID: DTXSID20912196
• Nikkaji Number: J1.444.199I
• Mol file: 69355-99-3.mol

Synonyms:Boc-D-Thr(Bzl)-OH;69355-99-3;Boc-O-benzyl-D-threonine;(2R,3S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid;O-Benzyl-N-(tert-butoxycarbonyl)-D-threonine;(2R,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoic acid;(2R,3S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}butanoic acid;BOC-D-Thr(OBzl);N-Boc-D-Thr(Bzl)-OH;SCHEMBL1414711;DTXSID20912196;CTXPLTPDOISPTE-WCQYABFASA-N;CS-B0830;MFCD00038247;AKOS015924179;AM90229;AS-56869;HY-15400;Boc-D-Thr(Bzl)-OH, >=98.0% (TLC);EN300-314254;F11892;O-Benzyl-N-(tert-butyloxycarbonyl)-D-threonine;A836448;3-benzyloxy-2-(tert-butoxycarbonylamino)butanoic acid;(2R,3S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoicacid;(2R,3S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)butanoic acid;(2R,3S)-3-benzyloxy-2-(tert-butoxycarbonyl-amino)-butanoic acid;D-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-;N-alpha-t-Butyloxycarbonyl-O-benZyl-D-threonine (Boc-D-Thr(BZl)-OH)

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

Chemical Property:

• Appearance/Colour: white - off-white powder
• Vapor Pressure: 2.58E-09mmHg at 25°C
• Melting Point: 110-117 °C
• Refractive Index: 1.518
• 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.: Store at RT.
• 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-D-threonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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-D-Thr(Bzl)-OH, is an amino acid derivative that can be used in the synthesis of millepachine amino acid prodrugs with enhanced solubility as antitumor agents.

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

There total 1 articles about Boc-O-benzyl-D-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:

benzyl bromide (100-39-0) + (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxybutyric acid (2592-18-9,23082-29-3,23082-30-6,55674-67-4,85979-33-5,86748-77-8) → Boc-O-benzyl-D-threonine (69355-99-3)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) DMF, -15 deg C, 2 h, 2.) DMF, RT, 5 h;

DOI:10.1246/bcsj.68.1369

Reference yield: 96.0%

4-octylaniline (16245-79-7) + Boc-O-benzyl-D-threonine (69355-99-3) → [(1R,2S)-2-Benzyloxy-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester (868553-64-4)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2005.07.057

Reference yield: 95.0%

Boc-O-benzyl-D-threonine (69355-99-3) + 3-methoxy-4-(1,3-oxazol-5-yl)aniline (198821-79-3) → tert-butyl ((2R,3S)-3-(benzyloxy)-1-((3-methoxy-4-(oxazol-5-yl)phenyl)-amino)-1-oxobutan-2-yl)carbamate

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20 ℃; for 14h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c00472

upstream raw materials:

benzyl bromide

(2R,3S)-2-tert-butoxycarbonylamino-3-hydroxybutyric acid

Downstream raw materials:

(2S,3R)-3-benzyloxy-2-(t-butoxycarbonyl)amino-1-butanol

(2S,3S)-3-((2R,3S)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyryloxy)-4-methyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-pentanoic acid allyl ester

(2R,3S)-3-benzyloxy-2-[tert-butoxycarbonyl-(methyl)-amino]-butanoic acid

[(1R,2S)-2-Benzyloxy-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester

Refernces