(4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate

Base Information

• Chemical Name: (4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate
• CAS No.: 1415635-75-4
• Molecular Formula: C₄₃H₆₄O₈Si
• Molecular Weight: 737.062
• Mol file: 1415635-75-4.mol

Synonyms:(4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate

Chemical Property of (4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate

There total 14 articles about (4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate 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: 81.0%

(S)-N-methoxy-N,2-dimethylpent-4-enamide (1012367-44-0) + (4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-methylbenzoate → (4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate (1415635-75-4)

Guidance literature:

(4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-methylbenzoate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;

(S)-N-methoxy-N,2-dimethylpent-4-enamide; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/ol302999v

Reference yield:

(2S)-N-[1R,2R]-(2-hydroxy-1-methyl-2-phenylethyl)-N,2-dimethyl-4-pentenamide (277297-37-7) → (4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate (1415635-75-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetra(n-butyl)ammonium hydroxide / tert-butyl alcohol; water / 23 h / 50 °C / Inert atmosphere; Reflux

2.1: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

2.2: 1 h / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

3.2: 0.17 h / -78 °C / Inert atmosphere

With 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; tetra(n-butyl)ammonium hydroxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ol302999v

Reference yield:

1-({[(2Z)-4-bromobut-2-en-1-yl]oxy}methyl)-4-methoxybenzene → (4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2,4-dimethoxy-6-((S)-3-methyl-2-oxopent-4-en-1-yl)benzoate (1415635-75-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: lithium chloride; diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 - 20 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran; hexane; ethyl acetate / 1 h / -78 - 0 °C / Inert atmosphere

3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.67 h / -78 - 20 °C / Inert atmosphere

3.2: 3 h / -78 °C / Inert atmosphere

3.3: 3 h / -116 °C / Inert atmosphere

4.1: tetra(n-butyl)ammonium hydroxide / tert-butyl alcohol; water / 20 h / 50 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

5.2: 1 h / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

8.1: diethyl ether / 3 h / -78 °C / Inert atmosphere

8.2: 4 h / Inert atmosphere; Reflux

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

9.2: 0.5 h / 0 - 20 °C / Inert atmosphere

10.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

10.2: 0.17 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; tetra(n-butyl)ammonium hydroxide; diisobutylaluminium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ol302999v

upstream raw materials:

(2S)-N-[1R,2R]-(2-hydroxy-1-methyl-2-phenylethyl)-N,2-dimethyl-4-pentenamide

(S)-2-methyl-4-pentenoic acid

(S)-N-methoxy-N,2-dimethylpent-4-enamide

(R,Z)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-6-((4-methoxybenzyl)oxy)-N,2-dimethylhex-4-enamide

Downstream raw materials:

(4S,5R,6R,7R,Z)-6-((tert-butyldimethylsilyl)oxy)-11-((4-methoxybenzyl)oxy)-5,7-dimethylundeca-1,9-dien-4-yl 2-((2R,3S)-2-hydroxy-3-methylpent-4-en-1-yl)-4,6-dimethoxybenzoate