Zizyphine A

Base Information

• Chemical Name: Zizyphine A
• CAS No.: 51059-42-8
• Molecular Formula: C₃₃H₄₉N₅O₆
• Molecular Weight: 611.782
• DSSTox Substance ID: DTXSID60422522
• Wikidata: Q27108592
• Metabolomics Workbench ID: 143800
• Mol file: 51059-42-8.mol

Synonyms:zizyphine A;zizyphine-A

Chemical Property of Zizyphine A

Chemical Property:

• Boiling Point: 844.8°Cat760mmHg
• Flash Point: 464.7°C
• PSA: 127.50000
• Density: 1.21g/cm³
• LogP: 3.63420
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 611.36828430
• Heavy Atom Count: 44
• Complexity: 1070

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)N1CCC2C1C(=O)N3CCCC3C(=O)NC=CC4=C(C=C(O2)C=C4)OC)NC(=O)C(C(C)CC)N(C)C
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)N1CC[C@H]2[C@H]1C(=O)N3CCC[C@H]3C(=O)N/C=C\C4=C(C=C(O2)C=C4)OC)NC(=O)[C@H]([C@@H](C)CC)N(C)C

Technology Process of Zizyphine A

There total 18 articles about Zizyphine A 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: 54.0%

N,N-dimethyl-L-isoleucine pentafluorophenyl ester (86272-78-8) + Cyclo-4-methoxyphenyl>oxy>-N-isoleucyl-(2S,3S)-prolyl>-(S)-prolyl> → Zizyphine A (51059-42-8)

Guidance literature:

With dmap; In 1,4-dioxane; at 80 ℃; for 7h;

DOI:10.1021/jo00164a010

Reference yield:

benzyl prolinate hydrochloride (80089-24-3) → Zizyphine A (51059-42-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 46.5 percent / N-methylmorpholine, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂

2: 1.) H₂ / 1.) Pd/C / 1.) 1h; 2.) ethyl acetate/methanol, diethyl ether

3: 1.) m-dimethoxybenzene; 2.) di-tert-butyl dicarbonate, 1N KHCO₃ / 1.) trifluoroacetic acid, 0 deg C, 3h; 2.) dioxane

4: 87 percent / N,N-carbonyldiimidazole / tetrahydrofuran / 5 h / 50 °C

5: 88 percent / NaNO₂ / acetic acid; H₂O / 0 °C

6: 1.)H₂; 2.) 1N KHCO₃ / 1.) Pd/C / 1.) acetic acid, 5h; 2.) dioxane, room temp.

7: 98 percent / NaCNBH₃ / tetrahydrofuran; acetic acid

8: 83 percent / 1N LiOH / dioxane

9: 90 percent / DCC / ethyl acetate / 1.) 0 deg C, 1h; 2.) room temp., 1h

10: 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; ethanol / 4 h

11: 72 percent / tributylphosphine / tetrahydrofuran / 2 h / Ambient temperature

12: 90 percent / 30percent H₂O₂ / CH₂Cl₂; pyridine; H₂O / 1 h / Ambient temperature

13: 92 percent / m-dimethoxybenzene / trifluoroacetic acid / Ambient temperature

14: 71 percent / DCC / CH₂Cl₂ / 4 h / Ambient temperature

15: m-dimethoxybenzene / trifluoroacetic acid / 0.5 h / Ambient temperature

16: 54 percent / 4-(dimethylamino)pyridine / dioxane / 7 h / 80 °C

With 4-methyl-morpholine; dmap; lithium hydroxide; tributylphosphine; di-tert-butyl dicarbonate; hydrogen; dihydrogen peroxide; sodium cyanoborohydride; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; 1,3-Dimethoxybenzene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dichloromethane; water; acetic acid; ethyl acetate; trifluoroacetic acid;

DOI:10.1021/jo00164a010

Reference yield:

trans-N-(tert-Butoxycarbonyl)-3-<<3-(tert-butoxycarbonyl)-4-methoxyphenyl>oxy>proline (86272-66-4) → Zizyphine A (51059-42-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 46.5 percent / N-methylmorpholine, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂

2: 1.) H₂ / 1.) Pd/C / 1.) 1h; 2.) ethyl acetate/methanol, diethyl ether

3: 1.) m-dimethoxybenzene; 2.) di-tert-butyl dicarbonate, 1N KHCO₃ / 1.) trifluoroacetic acid, 0 deg C, 3h; 2.) dioxane

4: 87 percent / N,N-carbonyldiimidazole / tetrahydrofuran / 5 h / 50 °C

5: 88 percent / NaNO₂ / acetic acid; H₂O / 0 °C

6: 1.)H₂; 2.) 1N KHCO₃ / 1.) Pd/C / 1.) acetic acid, 5h; 2.) dioxane, room temp.

7: 98 percent / NaCNBH₃ / tetrahydrofuran; acetic acid

8: 83 percent / 1N LiOH / dioxane

9: 90 percent / DCC / ethyl acetate / 1.) 0 deg C, 1h; 2.) room temp., 1h

10: 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; ethanol / 4 h

11: 72 percent / tributylphosphine / tetrahydrofuran / 2 h / Ambient temperature

12: 90 percent / 30percent H₂O₂ / CH₂Cl₂; pyridine; H₂O / 1 h / Ambient temperature

13: 92 percent / m-dimethoxybenzene / trifluoroacetic acid / Ambient temperature

14: 71 percent / DCC / CH₂Cl₂ / 4 h / Ambient temperature

15: m-dimethoxybenzene / trifluoroacetic acid / 0.5 h / Ambient temperature

16: 54 percent / 4-(dimethylamino)pyridine / dioxane / 7 h / 80 °C

With 4-methyl-morpholine; dmap; lithium hydroxide; tributylphosphine; di-tert-butyl dicarbonate; hydrogen; dihydrogen peroxide; sodium cyanoborohydride; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; 1,3-Dimethoxybenzene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dichloromethane; water; acetic acid; ethyl acetate; trifluoroacetic acid;

DOI:10.1021/jo00164a010

upstream raw materials:

N,N-dimethyl-L-isoleucine pentafluorophenyl ester

benzyl prolinate hydrochloride

C₁₉H₂₃N₃O₄

trans-N-(tert-Butoxycarbonyl)-3-<<3-(tert-butoxycarbonyl)-4-methoxyphenyl>oxy>proline

Refernces

• 1、 Schmidt, Ulrich,Lieberknecht, Albrecht,Boekens, Hilmar,Griesser, Helmut. "Totalsynthese von Zizyphin A und N-Acetylzizyphin B". . p. 1121 - 1122. Retrieved 2007/10/02.