N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide
• CAS No.: 143371-29-3
• Molecular Formula: C₆₂H₈₃NO₈SSi₂
• Molecular Weight: 1058.58

Synonyms:

Chemical Property of N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

There total 23 articles about N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide 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:

{(S)-3-[(4-Methoxy-benzyl)-(toluene-4-sulfonyl)-amino]-3-phenyl-propyl}-triphenyl-phosphonium; iodide (124944-47-4) → N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide (143371-29-3,143441-74-1)

Guidance literature:

Multi-step reaction with 9 steps

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

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

3: 95 percent / CH₃COOH, H₂O / tetrahydrofuran / 1 h / Ambient temperature

4: 81 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: 95 percent / imidazole, 4-pyrrolidinopyridine / dimethylformamide / 18 h

8: 88 percent / HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 5 h

9: 1.) lithium diisopropylamide (LDA) / 1.) THF, hexane, -78 deg C, 90 min, 2.) THF, hexane, -78 deg C, 40 min

With pyridine; 1H-imidazole; n-butyllithium; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium tert-butylate; water; sodium hydride; 4-pyrrolidin-1-ylpyridine; acetic acid; phenyllithium; mercury(II) oxide; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00047a008

Reference yield:

N-(4-Methoxy-benzyl)-4-methyl-N-[(S)-1-phenyl-3-(triphenyl-λ5-phosphanylidene)-propyl]-benzenesulfonamide → N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide (143371-29-3,143441-74-1)

Guidance literature:

Multi-step reaction with 8 steps

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

2: 95 percent / CH₃COOH, H₂O / tetrahydrofuran / 1 h / Ambient temperature

3: 81 percent / pyridine / 48 h / Ambient temperature

4: 97 percent / NaH, 18-crown-6 / tetrahydrofuran / 3 h

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

6: 95 percent / imidazole, 4-pyrrolidinopyridine / dimethylformamide / 18 h

7: 88 percent / HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 5 h

8: 1.) lithium diisopropylamide (LDA) / 1.) THF, hexane, -78 deg C, 90 min, 2.) THF, hexane, -78 deg C, 40 min

With pyridine; 1H-imidazole; n-butyllithium; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium tert-butylate; water; sodium hydride; 4-pyrrolidin-1-ylpyridine; acetic acid; phenyllithium; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00047a008

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide (143371-29-3,143441-74-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / CBr₄, PPh₃ / tetrahydrofuran / 2 h

2: diisobutylaluminum hydride (DIBAL) / CH₂Cl₂; hexane / 0.5 h / -78 °C

3: 1.) lithium diisopropylamide (LDA) / 1.) THF, 0 deg C, 10 min, 2.) THF, hexane, 0 deg C, 1 h

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

5: 95 percent / imidazole, 4-pyrrolidinopyridine / dimethylformamide / 18 h

6: 88 percent / HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 5 h

7: 1.) lithium diisopropylamide (LDA) / 1.) THF, hexane, -78 deg C, 90 min, 2.) THF, hexane, -78 deg C, 40 min

With 1H-imidazole; n-butyllithium; carbon tetrabromide; boron trifluoride diethyl etherate; diisobutylaluminium hydride; 4-pyrrolidin-1-ylpyridine; triphenylphosphine; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00047a008

upstream raw materials:

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

maleic anhydride

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

{(S)-3-[(4-Methoxy-benzyl)-(toluene-4-sulfonyl)-amino]-3-phenyl-propyl}-triphenyl-phosphonium; iodide

Downstream raw materials:

N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-2,3-dimethoxy-cyclopent-1-enyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-oxo-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

N-[(Z)-(1S,7S)-9-{(3S,5R)-5-[(Z)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-3-methoxy-2-oxo-cyclopentyl}-7-(tert-butyl-diphenyl-silanyloxy)-9-oxo-1-phenyl-non-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

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