Boc-asu-OH

Base Information

• Chemical Name: Boc-asu-OH
• CAS No.: 66713-87-9
• Molecular Formula: C₁₃H₂₃NO₆
• Molecular Weight: 289.329
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID70452294
• Nikkaji Number: J582.209B
• Wikidata: Q82272832
• Mol file: 66713-87-9.mol

Synonyms:BOC-ASU-OH;66713-87-9;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]octanedioic Acid;boc-d-asu-oh;(2S)-2-[(tert-butoxycarbonyl)amino]octanedioic acid;Boc-L-alpha-aminosuberic acid;SCHEMBL4409723;DTXSID70452294;(S)-2-(tert-butoxycarbonylamino)octanedioic acid;(S)-2-[(tert-Butoxycarbonyl)amino]suberic acid;(S)-2-((tert-Butoxycarbonyl)amino)octanedioic acid;Octanedioicacid,2-[[(1,1-dimethylethoxy)carbonyl]amino]-,(2S)-

Chemical Property of Boc-asu-OH

Chemical Property:

• Melting Point: 118 °C
• Boiling Point: 486.1±40.0 °C(Predicted)
• PKA: 4.00±0.21(Predicted)
• PSA: 112.93000
• Density: 1.180±0.06 g/cm3(Predicted)
• LogP: 2.39030
• Storage Temp.: Store at 0-5°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 289.15253745
• Heavy Atom Count: 20
• Complexity: 347

Purity/Quality:

98%Min ^*data from raw suppliers

Boc-Asu-OH ^*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(CCCCCC(=O)O)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCCCCC(=O)O)C(=O)O

Technology Process of Boc-asu-OH

There total 5 articles about Boc-asu-OH 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%

di-tert-butyl dicarbonate (24424-99-5) + (2S)-L-α-Aminosuberic acid (4254-88-0,19641-59-9) → (2S)-N-tert-butoxycarbonyl-2-aminosuberic acid (66713-87-9,75113-71-2)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 1h;

DOI:10.1021/ja209018u

Reference yield:

ethyl (2E)-2,9-decadienoate (78426-45-6) → (2S)-N-tert-butoxycarbonyl-2-aminosuberic acid (66713-87-9,75113-71-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / diisobutyl aluminum hydride / diethyl ether; hexane / 1 h / 0 °C

2: 1.) diisopropyl D-(-)-tartrate, titanium tetraisopropoxide, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -22 deg C, 1 h, 2.) CH₂Cl₂, isooctane, -20 deg C, 20 h

3: 68 percent / titanium tetraisopropoxide / CH₂Cl₂ / 24 h / Heating

4: 1.) NaIO₄, RuCl₃, 2.) NaHCO₃ / 1.) CH₃CN, CCl₄, water, room temp., 17 h, 2.) methanol, ultrasonic irrad., room temp., 15 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium trichloride; sodium periodate; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; In diethyl ether; hexane; dichloromethane;

DOI:10.1080/00397919408011722

Reference yield:

(2E)-deca-2,9-dien-1-ol (156360-46-2) → (2S)-N-tert-butoxycarbonyl-2-aminosuberic acid (66713-87-9,75113-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) diisopropyl D-(-)-tartrate, titanium tetraisopropoxide, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -22 deg C, 1 h, 2.) CH₂Cl₂, isooctane, -20 deg C, 20 h

2: 68 percent / titanium tetraisopropoxide / CH₂Cl₂ / 24 h / Heating

3: 1.) NaIO₄, RuCl₃, 2.) NaHCO₃ / 1.) CH₃CN, CCl₄, water, room temp., 17 h, 2.) methanol, ultrasonic irrad., room temp., 15 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium trichloride; sodium periodate; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; In dichloromethane;

DOI:10.1080/00397919408011722

upstream raw materials:

di-tert-butyl dicarbonate

(2S,3S)-N-diphenylmethyl-3-amino-9-decen-1,2-diol

(2S)-L-α-Aminosuberic acid

ethyl (2E)-2,9-decadienoate

Refernces

• 1、 Liu, Tao,Kapustin, Galina,Etzkorn, Felicia A.. "Design and synthesis of a potent histone deacetylase inhibitor". . p. 2003 - 2006. Retrieved 2008/02/01.