Nalpha,Nepsilon-bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester

Base Information

• Chemical Name: Nalpha,Nepsilon-bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester
• CAS No.: 97347-40-5
• Molecular Formula: C₂₀H₃₆N₂O₇
• Molecular Weight: 416.515
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID00452828
• Nikkaji Number: J977.777F
• Wikidata: Q82273675
• Mol file: 97347-40-5.mol

Synonyms:97347-40-5;Nalpha,Nepsilon-bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester;tert-butyl (2S)-2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohexanoate;DTXSID00452828;N|A,N|A-bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester;KOLDSECLRRRIFP-ZDUSSCGKSA-N;AKOS030255221;N?,N?-bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester;tert-Butyl N~2~,N~6~-bis(tert-butoxycarbonyl)-6-oxo-L-lysinate;N alpha ,N epsilon -bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester;N-(tert-Butoxycarbonyl)-6-oxo-6-(tert-butoxycarbonylamino)-L-norleucine tert-butyl ester

Chemical Property of Nalpha,Nepsilon-bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester

Chemical Property:

• Refractive Index: 1.469
• PKA: 8.32±0.46(Predicted)
• PSA: 120.03000
• Density: 1.084g/cm³
• LogP: 4.22480
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 416.25225149
• Heavy Atom Count: 29
• Complexity: 595

Purity/Quality:

97% ^*data from raw suppliers

Nα,Nε-bis-Boc-L-2-aminoadipamicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Nalpha,Nepsilon-bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester

There total 3 articles about Nalpha,Nepsilon-bis-Boc-L-2-aminoadipamic Acid tert-Butyl Ester 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: 86.0%

Boc-Lys(Boc)-Otert-Bu (97347-28-9) → Nα,Nca-diBoc-L-2-aminoadipamic acid tert-butyl ester (97347-40-5) + (S)-6-tert-Butoxycarbonylamino-piperidine-1,2-dicarboxylic acid di-tert-butyl ester

Guidance literature:

With ruthenium(IV) oxide; sodium bromate; In water; ethyl acetate; 5.5 h, 45 deg C, then 18 h, RT;

DOI:10.1016/S0040-4039(98)01142-3

Reference yield: 8.0%

Boc-Lys(Boc)-Otert-Bu (97347-28-9) → Nα,Nca-diBoc-L-2-aminoadipamic acid tert-butyl ester (97347-40-5) + N-Boc-6-tert-butoxycarbonylaminopiperidine-2-carboxylic acid tert-butyl ester (114659-53-9)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In ethyl acetate; for 6h; Ambient temperature;

Reference yield:

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) → Nα,Nca-diBoc-L-2-aminoadipamic acid tert-butyl ester (97347-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOH, 2.) BF₃*Et₂O / 1.) dioxane, H₂O, 2.) c-hexane, CH₂Cl₂

2: 86 percent / NaBrO₃, RuO₂ / ethyl acetate; H₂O / 5.5 h, 45 deg C, then 18 h, RT

With ruthenium(IV) oxide; sodium hydroxide; sodium bromate; boron trifluoride diethyl etherate; In water; ethyl acetate;

DOI:10.1016/S0040-4039(98)01142-3

upstream raw materials:

Boc-Lys(Boc)-Otert-Bu

tert-Butyl 2,2,2-trichloroacetimidate

Downstream raw materials:

L-homoglutamic acid

(S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-6-hydroxy-(S)-norleucine methyl ester

(S)-2-amino-6-hydroxy-hexanoic acid methyl ester

L-2-aminoadipamic acid