(4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione

Base Information

• Chemical Name: (4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione
• CAS No.: 124944-57-6
• Molecular Formula: C₄₆H₅₃NO₇
• Molecular Weight: 731.929

Synonyms:(4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione

Chemical Property of (4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione

There total 37 articles about (4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione 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: 69.0%

{(E)-3-[[(E)-(1S,7S)-9-[(3S,5R)-2,3-Dimethoxy-5-((Z)-2-methyl-3-oxo-propenyl)-cyclopent-1-enyl]-7-(4-methoxy-benzyloxy)-9-oxo-1-phenyl-non-3-enyl]-(4-methoxy-benzyl)-carbamoyl]-allyl}-phosphonic acid diethyl ester (124944-56-5) → (4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione (124944-57-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1021/jo00291a005

Reference yield:

{(S)-3-[(4-Methoxy-benzyl)-(toluene-4-sulfonyl)-amino]-3-phenyl-propyl}-triphenyl-phosphonium; iodide (124944-47-4) → (4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione (124944-57-6)

Guidance literature:

Multi-step reaction with 18 steps

1: n-butyllithium, LiBr / tetrahydrofuran / 0.75 h / 0 °C

2: 2.) phenyllithium, 3.) t-BuOK

3: 96 percent / CH₃COOH, H₂O / tetrahydrofuran / 1 h / Ambient temperature

4: 80 percent / pyridine / 48 h / Ambient temperature

5: 97 percent / NaH, 18-crown-6 / tetrahydrofuran / 3 h

6: 1.) n-butyllithium / 1.) THF, hexane, -23 deg C, 80 min, 2.) THF, hexane, 5 min

7: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min

8: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C

9: 99 percent / K₂CO₃ / tetrahydrofuran; toluene

10: 85 percent / MeI, H₂O / acetonitrile / Ambient temperature

11: 1.) t-BuLi, 2.) dineopentylzinc

12: (CH₃)2SO, pyridine, CF₃COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature

13: benzene; diethyl ether / 0.33 h

14: n-Bu₄NF / tetrahydrofuran / 0.25 h / 0 °C

15: 75percent aq. CH₃COOH / tetrahydrofuran / 0 - 5 °C

16: 68 percent / diethyl cyanophosphonate, Et₃N / dimethylformamide / 0.5 h / 0 °C

17: 86 percent / (COCl)2, (CH₃)2SO / CH₂Cl₂ / 0.33 h / -78 °C

18: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C

With pyridine; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; diethyl cyanophosphonate; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; water; tert.-butyl lithium; potassium hydride; sodium naphthalenide; sodium hydride; dineopentylzinc; potassium carbonate; acetic acid; dimethyl sulfoxide; phenyllithium; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium bromide; lithium hexamethyldisilazane; methyl iodide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1021/ja00047a008

Reference yield:

N-(4-Methoxy-benzyl)-4-methyl-N-((E)-(S)-6-(S)-oxiranyl-1-phenyl-hex-3-enyl)-benzenesulfonamide (124944-48-5) → (4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,2-Dimethoxy-11-(4-methoxy-benzyl)-18-(4-methoxy-benzyloxy)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione (124944-57-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) n-butyllithium / 1.) THF, hexane, -23 deg C, 80 min, 2.) THF, hexane, 5 min

2: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min

3: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C

4: 99 percent / K₂CO₃ / tetrahydrofuran; toluene

5: 85 percent / MeI, H₂O / acetonitrile / Ambient temperature

6: 1.) t-BuLi, 2.) dineopentylzinc

7: (CH₃)2SO, pyridine, CF₃COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature

8: benzene; diethyl ether / 0.33 h

9: n-Bu₄NF / tetrahydrofuran / 0.25 h / 0 °C

10: 75percent aq. CH₃COOH / tetrahydrofuran / 0 - 5 °C

11: 68 percent / diethyl cyanophosphonate, Et₃N / dimethylformamide / 0.5 h / 0 °C

12: 86 percent / (COCl)2, (CH₃)2SO / CH₂Cl₂ / 0.33 h / -78 °C

13: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C

With pyridine; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; water; tert.-butyl lithium; potassium hydride; sodium naphthalenide; dineopentylzinc; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; methyl iodide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1021/ja00047a008

upstream raw materials:

{(E)-3-[[(E)-(1S,7S)-9-[(3S,5R)-2,3-Dimethoxy-5-((Z)-2-methyl-3-oxo-propenyl)-cyclopent-1-enyl]-7-(4-methoxy-benzyloxy)-9-oxo-1-phenyl-non-3-enyl]-(4-methoxy-benzyl)-carbamoyl]-allyl}-phosphonic acid diethyl ester

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

maleic anhydride

(S)-(-)-5-methoxycyclopent-2-en-1-one

Downstream raw materials:

(4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,18-Dihydroxy-2-methoxy-11-(4-methoxy-benzyl)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione

(+)-hitachimycin

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