Boc-L-beta-homotryptophan

Base Information

• Chemical Name: Boc-L-beta-homotryptophan
• CAS No.: 229639-48-9
• Molecular Formula: C17H22 N2 O4
• Molecular Weight: 318.37
• DSSTox Substance ID: DTXSID40375825
• Nikkaji Number: J1.257.941A
• Wikidata: Q72470032
• Mol file: 229639-48-9.mol

Synonyms:229639-48-9;Boc-L-beta-homotryptophan;(S)-3-((tert-Butoxycarbonyl)amino)-4-(1H-indol-3-yl)butanoic acid;N-beta-Boc-L-Homotryptophan;(3S)-4-(1H-indol-3-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;Boc-L-beta-HTrp-OH;Boc-b-HoTrp-OH;MFCD01862938;Boc-Trp-(C#CH2)OH;1H-Indole-3-butanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-, (betaS)-;SCHEMBL5467203;DTXSID40375825;AKOS024462373;DS-7833;AC-22097;Boc-beta-Homotrp-OH, >=98.0% (TLC);CS-0154489;A816449;(S)-3-((tert-Butoxycarbonyl)amino)-4-(1H-indol-3-yl)butanoicacid;(S)-3-(tert-butoxycarbonylamino)-4-(1H-indol-3-yl)butanoic acid;(S)-beta-[(tert-Butyloxycarbonyl)amino]-1H-indole-3-butyric acid

Chemical Property of Boc-L-beta-homotryptophan

Chemical Property:

• Vapor Pressure: 6.21E-13mmHg at 25°C
• Melting Point: ?11-?9°C(lit.)
• Boiling Point: 550.1°Cat760mmHg
• PKA: 4.50±0.10(Predicted)
• Flash Point: 286.5°C
• PSA: 91.42000
• Density: 1.235g/cm³
• LogP: 3.46930
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 318.15795719
• Heavy Atom Count: 23
• Complexity: 433

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-L-beta-homotryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)CC(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)CC(=O)O
• Uses: Boc-l-beta-homotryptophan

Technology Process of Boc-L-beta-homotryptophan

There total 6 articles about Boc-L-beta-homotryptophan 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: 89.0%

tert-butyl N-{(1S)-3-diazo-1-[(1H-3-indolyl)methyl]-2-oxopropyl}carbamate (72621-31-9) → (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-(1H-indol-3-yl)butanoic acid (229639-48-9)

Guidance literature:

With water; triethylamine; silver trifluoroacetate; In tetrahydrofuran;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1223::AID-ANIE1223>3.0.CO;2-A

Reference yield: 29.3%

tert-butyl [(1S)-2-cyano-1-(1H-indol-3-ylmethyl)ethyl]carbamate (1039025-39-2) → (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-(1H-indol-3-yl)butanoic acid (229639-48-9)

Guidance literature:

With potassium hydroxide; In ethanol; for 9h; Heating;

DOI:10.1248/cpb.56.260

Reference yield:

Boc-Trp-OH (13139-14-5) → (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-(1H-indol-3-yl)butanoic acid (229639-48-9)

Guidance literature:

Multi-step reaction with 3 steps

1: TEA / tetrahydrofuran / 0.25 h / -15 °C

2: tetrahydrofuran / 1 h / -5 °C

3: aq. CF₃COOAg; TEA / tetrahydrofuran / 4 h / 20 °C

With TEA; silver trifluoroacetate; In tetrahydrofuran;

DOI:10.1021/jm011059z

upstream raw materials:

tert-butyl N-{(1S)-3-diazo-1-[(1H-3-indolyl)methyl]-2-oxopropyl}carbamate

Boc-Trp-OH

[1-chlorocarbonyl-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

tert-butyl [(1S)-2-cyano-1-(1H-indol-3-ylmethyl)ethyl]carbamate

Downstream raw materials:

N_β-tert-butoxycarbonyl-L-β-homotryptophan methyl ester

Refernces

• 1、 Mukai, Takahiro,Suganuma, Noriko,Soejima, Kenta,Sasaki, Junichi,Yamamoto, Fumihiko,Maeda, Minoru. "Synthesis of a β-tetrapeptide analog as a mother compound for the development of matrix metalloproteinase-2-imaging agents". . p. 260 - 265. Retrieved 2008/09/21.
• 2、 Linder, Michael R.,Steurer, Steffen,Podlech, Joachim. "(S)-3-(tert-butyloxycarbonylamino)-4-phenylbutanoic acid [ [Benzenebutanoic acid, β-[[(1,1-dimethylethoxy)carbonyl]amino]-, (S)-]". . p. 154 - 154. Retrieved 2017/09/20.