O-O-Dibenzyl-(-)-actinonin

Base Information

• Chemical Name: O-O-Dibenzyl-(-)-actinonin
• CAS No.: 460754-33-0
• Molecular Formula: C33H47N3O5
• Molecular Weight: 565.74338
• DSSTox Substance ID: DTXSID70458216
• Wikidata: Q82281407
• Mol file: 460754-33-0.mol

Synonyms:O-O-Dibenzyl-(-)-actinonin;460754-33-0;O,O-Dibenzyl (-)-Actinonin;(2R)-N-[(2S)-3-methyl-1-oxo-1-[(2S)-2-(phenylmethoxymethyl)pyrrolidin-1-yl]butan-2-yl]-2-pentyl-N'-phenylmethoxybutanediamide;(2R)-N1-[(1S)-2-Methyl-1-[[(2S)-2-[(phenylmethoxy)methyl]-1-pyrrolidinyl]carbonyl]propyl]-2-pentyl-N4-(phenylmethoxy)butanediamide;SCHEMBL6298387;DTXSID70458216;AKOS030242119;N4-Benzyloxy-N1-[1-(2-(S)-benzyloxy-methyl-pyrrolidine-1-carbonyl)-2-(S)-methyl-propyl]-2-(R)-pentylsuccinamide;CS-0145240;E81832;(R)-N4-(Benzyloxy)-N1-((S)-1-((S)-2-((benzyloxy)methyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-pentylsuccinamide

Chemical Property of O-O-Dibenzyl-(-)-actinonin

Chemical Property:

• PSA: 103.95000
• LogP: 6.78810
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 17
• Exact Mass: 565.35157161
• Heavy Atom Count: 41
• Complexity: 779

Purity/Quality:

97% ^*data from raw suppliers

O,O-Dibenzyl(-)-Actinonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CC(=O)NOCC1=CC=CC=C1)C(=O)NC(C(C)C)C(=O)N2CCCC2COCC3=CC=CC=C3
• Isomeric SMILES: CCCCC[C@H](CC(=O)NOCC1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)N2CCC[C@H]2COCC3=CC=CC=C3
• Uses: O,O-Dibenzyl (-)-Actinonin is an analog of (-)-Actinonin (A192000) as antitumor agent.

Technology Process of O-O-Dibenzyl-(-)-actinonin

There total 6 articles about O-O-Dibenzyl-(-)-actinonin 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: 79.0%

C30H48N2O5 + O-benzylhydoxylamine hydrochloride (2687-43-6) → C33H47N3O5 (460754-33-0)

Guidance literature:

C₃₀H₄₈N₂O₅; With trifluoroacetic acid; In dichloromethane; at 20 ℃;

O-benzylhydoxylamine hydrochloride; With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 3 - 5h; Concentration; Reagent/catalyst; Inert atmosphere; Cooling with ice;

Reference yield:

3-(1-(2-benzyloxymethyl-pyrrolidine-1-carbonyl)-2-methylpropylcarbamoyl)-octanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (460754-32-9) + N-benzylhydroxylamine hydrochloride (29601-98-7) → N4-benzyloxy-N1-(1-(2-(S)-benzyloxymethyl-pyrrolidine-1-carbonyl)-2-(S)-methyl-propyl)-2-(R)-pentylsuccinamide (460754-33-0)

Guidance literature:

With sodium hydrogencarbonate; In hexane; water; ethyl acetate; triethylamine; N,N-dimethyl-formamide;

Reference yield:

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → C33H47N3O5 (460754-33-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere; Cooling with ice

1.2: 0.25 h / 0 °C

2.1: trifluoroacetic acid / dichloromethane / 20 °C

2.2: 3 h / Inert atmosphere; Cooling with ice

3.1: trifluoroacetic acid / dichloromethane / 20 °C

3.2: 3 - 5 h / Inert atmosphere; Cooling with ice

4.1: trifluoroacetic acid / dichloromethane / 20 °C

4.2: 3 - 5 h / Inert atmosphere; Cooling with ice

With sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

3-(1-(2-benzyloxymethyl-pyrrolidine-1-carbonyl)-2-methylpropylcarbamoyl)-octanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

N-benzylhydroxylamine hydrochloride

O-benzylhydoxylamine hydrochloride

N-(tert-butoxycarbonyl)-L-prolinol

Downstream raw materials:

actinonin

Refernces

• 1、 -. "Analogs and derivatives of (S,S,R)-(-)-actinonin and uses therefor". . . Retrieved 2008/06/13.