calphostin A

Base Information

• Chemical Name: calphostin A
• CAS No.: 120461-92-9
• Molecular Formula: C₄₄H₃₈O₁₂
• Molecular Weight: 758.779
• Mol file: 120461-92-9.mol

Synonyms:AntibioticUCN 1028A; Calphostin A; UCN 1028A

Chemical Property of calphostin A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 989.2°Cat760mmHg
• Flash Point: 302.5°C
• PSA: 164.12000
• Density: 1.43g/cm³
• LogP: 7.36460

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of calphostin A

There total 24 articles about calphostin 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:

2-bromo-1,5-dimethoxy-3-methylbenzene (13321-73-8) → calphostin A (120461-92-9,132956-51-5)

Guidance literature:

Multi-step reaction with 26 steps

1: 1.) n-BuLi / 1.) Et₂O, 0 deg, 30 min

2: (COCl)2 / 0 - 20 °C

3: pyridine

4: BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C

5: NaH / dimethylformamide

6: 1.) LDA / 1.) THF, -78 deg, 10 min

7: DDQ / dioxane / 0.17 h / 60 °C

8: K₂CO₃ / dimethylsulfoxide / 16 h / 20 °C

9: LAH / tetrahydrofuran / 1 h / 0 °C

10: pyridine / 24 h

11: imidazole / dimethylformamide / 16 h / 0 - 20 °C

12: TsOH / CH₂Cl₂; methanol / 0.08 h

13: 62 percent / PCC / CH₂Cl₂ / 20 °C

14: 91 percent / NBS / CH₂Cl₂ / 0.5 h / 20 °C

15: MCPBA, Na₂SO₄, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C

16: aq. NaOH / methanol; tetrahydrofuran / 20 °C

17: K₂CO₃ / dimethylsulfoxide / 16 h / 20 °C

18: TBAF

19: DEAD, PPh₃

20: NaOH

22: 1.) t-BuLi, 2.) FeCl₃ / 1.) THF, -78 deg, 2.) -78 deg to 20 deg

23: 1.) TBAF, 2.) H₂ / 2.) Pd/C / 1.) THF, 2.) THF, MeOH

24: 65 percent / K₃Fe(CN)6, NaOH / H₂O; ethanol; tetrahydrofuran / 20 °C

25: 54 percent / DMAP, pyridine

26: aq. HCl

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; boron tribromide; iron(III) chloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); lithium diisopropyl amide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)92105-1

Reference yield:

2,4-dimethoxy-6-methylbenzoyl chloride (55018-89-8) → calphostin A (120461-92-9,132956-51-5)

Guidance literature:

Multi-step reaction with 24 steps

1: pyridine

2: BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C

3: NaH / dimethylformamide

4: 1.) LDA / 1.) THF, -78 deg, 10 min

5: DDQ / dioxane / 0.17 h / 60 °C

6: K₂CO₃ / dimethylsulfoxide / 16 h / 20 °C

7: LAH / tetrahydrofuran / 1 h / 0 °C

8: pyridine / 24 h

9: imidazole / dimethylformamide / 16 h / 0 - 20 °C

10: TsOH / CH₂Cl₂; methanol / 0.08 h

11: 62 percent / PCC / CH₂Cl₂ / 20 °C

12: 91 percent / NBS / CH₂Cl₂ / 0.5 h / 20 °C

13: MCPBA, Na₂SO₄, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C

14: aq. NaOH / methanol; tetrahydrofuran / 20 °C

15: K₂CO₃ / dimethylsulfoxide / 16 h / 20 °C

16: TBAF

17: DEAD, PPh₃

18: NaOH

20: 1.) t-BuLi, 2.) FeCl₃ / 1.) THF, -78 deg, 2.) -78 deg to 20 deg

21: 1.) TBAF, 2.) H₂ / 2.) Pd/C / 1.) THF, 2.) THF, MeOH

22: 65 percent / K₃Fe(CN)6, NaOH / H₂O; ethanol; tetrahydrofuran / 20 °C

23: 54 percent / DMAP, pyridine

24: aq. HCl

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; boron tribromide; iron(III) chloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); lithium diisopropyl amide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)92105-1

Reference yield:

ethyl everninate (6110-36-7) → calphostin A (120461-92-9,132956-51-5)

Guidance literature:

Multi-step reaction with 22 steps

1: NaH / dimethylformamide

2: 1.) LDA / 1.) THF, -78 deg, 10 min

3: DDQ / dioxane / 0.17 h / 60 °C

4: K₂CO₃ / dimethylsulfoxide / 16 h / 20 °C

5: LAH / tetrahydrofuran / 1 h / 0 °C

6: pyridine / 24 h

7: imidazole / dimethylformamide / 16 h / 0 - 20 °C

8: TsOH / CH₂Cl₂; methanol / 0.08 h

9: 62 percent / PCC / CH₂Cl₂ / 20 °C

10: 91 percent / NBS / CH₂Cl₂ / 0.5 h / 20 °C

11: MCPBA, Na₂SO₄, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C

12: aq. NaOH / methanol; tetrahydrofuran / 20 °C

13: K₂CO₃ / dimethylsulfoxide / 16 h / 20 °C

14: TBAF

15: DEAD, PPh₃

16: NaOH

18: 1.) t-BuLi, 2.) FeCl₃ / 1.) THF, -78 deg, 2.) -78 deg to 20 deg

19: 1.) TBAF, 2.) H₂ / 2.) Pd/C / 1.) THF, 2.) THF, MeOH

20: 65 percent / K₃Fe(CN)6, NaOH / H₂O; ethanol; tetrahydrofuran / 20 °C

21: 54 percent / DMAP, pyridine

22: aq. HCl

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; iron(III) chloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); lithium diisopropyl amide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)92105-1

upstream raw materials:

2-bromo-1,5-dimethoxy-3-methylbenzene

2,4-dimethoxy-6-methylbenzoyl chloride

ethyl everninate

ethyl 2,4-dimethoxy-6-methylbenzoate

Refernces