(2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide

Base Information

• Chemical Name: (2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide
• CAS No.: 1402974-93-9
• Molecular Formula: C₃₀H₅₁NO₃Si
• Molecular Weight: 501.825

Synonyms:(2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide

Chemical Property of (2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide

There total 6 articles about (2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide 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:

tert-butyl((2E,4R,5R,6E)-8-iodo-3,5,7-trimethylocta-2,6-dien-4-yloxy)dimethylsilane (134833-59-3) + N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) → (2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide (1402974-93-9)

Guidance literature:

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

tert-butyl((2E,4R,5R,6E)-8-iodo-3,5,7-trimethylocta-2,6-dien-4-yloxy)dimethylsilane; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 14h; Inert atmosphere;

DOI:10.1002/chem.201201879 DOI:10.1002/chem.201201879

Reference yield:

2-methylbut-2-enal (497-03-0) → (2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide (1402974-93-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: titanium tetrachloride / dichloromethane / 120 h / -78 - -50 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere

3.1: lithium borohydride / methanol; diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

4.1: methyltriphenoxyphosphonium iodide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere

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

5.2: 14 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium borohydride; n-butyllithium; methyltriphenoxyphosphonium iodide; titanium tetrachloride; diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: |Mukaiyama Aldol Addition;

DOI:10.1002/chem.201201879 DOI:10.1002/chem.201201879

Reference yield:

(R)-3-((2E,4R,5R,6E)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylocta-2,6-dienoyl)-4-isopropyloxazolidin-2-one (908333-86-8) → (2S,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8-pentamethyldeca-4,8-dienamide (1402974-93-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium borohydride / methanol; diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

2.1: methyltriphenoxyphosphonium iodide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere

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

3.2: 14 h / 0 - 20 °C / Inert atmosphere

With lithium borohydride; n-butyllithium; methyltriphenoxyphosphonium iodide; diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201201879 DOI:10.1002/chem.201201879

upstream raw materials:

(R)-3-((2E,4R,5R,6E)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylocta-2,6-dienoyl)-4-isopropyloxazolidin-2-one

2-methylbut-2-enal

(4R,1'E,3'E)-(-1'-{[tert-butyl(dimethyl)silyl]oxy}-2'-methyl-1',3'-pentadienyl)-4-isopropyl-1,3-oxazolidin-2-one

(R)-3-((2E,6E)-(4R,5R)-5-Hydroxy-2,4,6-trimethyl-octa-2,6-dienoyl)-4-isopropyl-oxazolidin-2-one

Downstream raw materials:

(2R,4R,6E,8R,9R,10E)-9-(tert-butyldimethylsilyloxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6,8,10-hexamethyldodeca-6,10-dienamide

(2R,4R,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate

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