CID 36642

Base Information

• Chemical Name: CID 36642
• CAS No.: 33956-61-5
• Deprecated CAS: 32576-01-5,11093-42-8,62975-29-5,85999-84-4,88452-61-3
• Molecular Formula: C₄₄H₇₂O₁₂
• Molecular Weight: 793.048
• European Community (EC) Number: 608-930-4
• Mol file: 33956-61-5.mol

Synonyms:tetranactin

Chemical Property of CID 36642

Chemical Property:

• Vapor Pressure: 1.65E-34mmHg at 25°C
• Boiling Point: 916.2°Cat760mmHg
• Flash Point: 357.2°C
• PSA: 142.12000
• Density: 1.019g/cm³
• LogP: 7.58240
• XLogP3: 8.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 792.50237773
• Heavy Atom Count: 56
• Complexity: 1100

Purity/Quality:

>95% by HPLC ^*data from raw suppliers

Tetranactin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CC2CCC(O2)C(C(=O)OC(CC3CCC(O3)C(C(=O)OC(CC4CCC(O4)C(C(=O)OC(CC5CCC(O5)C(C(=O)O1)C)CC)C)CC)C)CC)C
• Uses: Tetranactin is a member of the macrotetrolide complex produced by a range of Streptomyces sp.. Like the other members of the macrotetrolide family, tetranactin is thought to act as a monovalent cation ionophore with high selectivity for ammonium and potassium. Unlike the other macrotetrolides, tetranactin exhibits potent insecticidal activity. Tetranactin is a monvalent cation ionophore with high selectivity for ammonium and potassium.

Technology Process of CID 36642

There total 18 articles about CID 36642 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: 51.0%

(-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-S-(3-cyano-4,6-dimethyl-2-pyridinylester) (110881-06-6) → Tetranactin (33956-61-5,32576-01-5,62975-29-5,88452-61-3)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 4.5h; Heating;

DOI:10.1055/s-1986-31846

Reference yield:

(furan-2-yl)ethylene (1487-18-9) → Tetranactin (33956-61-5,32576-01-5,62975-29-5,88452-61-3)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) m-tolyl-lithium / 2.) THF, 5 deg C, 4 h, to room temp.

2: 0.5 h

3: 90 percent / TPP, H₂ / 2 / 24 h / 70 °C / 76000 Torr

4: NaClO₂, H₂N-SO₃H, Na₂HPO₄ / dioxane; H₂O / 0.5 h / Ambient temperature

5: KOH / methanol / 0.5 h / Ambient temperature

6: diethyl ether / 0.03 h / Ambient temperature

7: H₂ / 5percent Rh/Al₂O₃ / methanol / 1.5 h / 2280 Torr / Ambient temperature

8: KOH / methanol / 0.5 h / Ambient temperature

9: 1.) KHCO₃ / 1.) H₂O, 2.) DMSO, 50 deg C, 16 h

10: 96 percent / imidazole / dimethylformamide / 1 h / 50 °C

11: H₂ / 5percent Pd/C / tetrahydrofuran / 1 h / Ambient temperature

12: Me₂C=C(Cl)NMe₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

13: 4-pyrrolidinopyridine / CH₂Cl₂ / 2 h / Ambient temperature

14: 94 percent / 40percent aq. HF / acetonitrile / 1 h / Ambient temperature

15: H₂ / 5percent Pd/C / tetrahydrofuran / 1 h / Ambient temperature

16: 71 percent / TPP / toluene / 1.5 h

17: 51 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 4 h / Heating

With 1H-imidazole; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; aminosulfonic acid; hydrogen fluoride; hydrogen; thiamine diphosphate; m-tolyllithium; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; palladium on activated charcoal; Rh/Al₂O₃; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/c39860000996

Reference yield:

2-[5-((S)-2-Hydroxy-butyl)-furan-2-yl]-propionic acid → Tetranactin (33956-61-5,32576-01-5,62975-29-5,88452-61-3)

Guidance literature:

Multi-step reaction with 12 steps

1: diethyl ether / 0.03 h / Ambient temperature

2: H₂ / 5percent Rh/Al₂O₃ / methanol / 1.5 h / 2280 Torr / Ambient temperature

3: KOH / methanol / 0.5 h / Ambient temperature

4: 1.) KHCO₃ / 1.) H₂O, 2.) DMSO, 50 deg C, 16 h

5: 96 percent / imidazole / dimethylformamide / 1 h / 50 °C

6: H₂ / 5percent Pd/C / tetrahydrofuran / 1 h / Ambient temperature

7: Me₂C=C(Cl)NMe₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

8: 4-pyrrolidinopyridine / CH₂Cl₂ / 2 h / Ambient temperature

9: 94 percent / 40percent aq. HF / acetonitrile / 1 h / Ambient temperature

10: H₂ / 5percent Pd/C / tetrahydrofuran / 1 h / Ambient temperature

11: 71 percent / TPP / toluene / 1.5 h

12: 51 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 4 h / Heating

With 1H-imidazole; potassium hydroxide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; hydrogen fluoride; hydrogen; thiamine diphosphate; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; palladium on activated charcoal; Rh/Al₂O₃; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/c39860000996

upstream raw materials:

(-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-S-(3-cyano-4,6-dimethyl-2-pyridinylester)

(furan-2-yl)ethylene

2-<2(S)-Acetoxybutyl>-5-vinylfuran

5-<(2S)-Hydroxybutyl>-α(R,S)-methylfuran-2-essigsaeure-methylester