10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester

Base Information

• Chemical Name: 10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester
• CAS No.: 869226-99-3
• Molecular Formula: C₂₇H₃₆O₅Si
• Molecular Weight: 468.665
• Mol file: 869226-99-3.mol

Synonyms:10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester

Chemical Property of 10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester

There total 1 articles about 10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester 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: 64.0%

acetoacetic acid methyl ester (105-45-3) + 6-(tert-butyl(diphenyl)silanyloxy)-hex-2-enal (153361-01-4) → 10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester (869226-99-3)

Guidance literature:

acetoacetic acid methyl ester; With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; at 0 ℃;

6-(tert-butyl(diphenyl)silanyloxy)-hex-2-enal; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

DOI:10.1021/jo051318i

Reference yield:

10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester (869226-99-3) → 10-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-dec-6-enoic acid methyl ester

Guidance literature:

With tetramethylammonium borohydride; acetic acid; In acetonitrile; at -25 ℃; for 15h;

DOI:10.1021/jo051318i

Reference yield:

10-(tert-butyl(diphenyl)silanyloxy)-5-hydroxy-3-oxo-dec-6-enoic acid methyl ester (869226-99-3) → (Z)-(1R,2R,6S,8S,9R,13R)-4-Benzyl-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-13-hydroxy-4-aza-tricyclo[6.5.1.02,6]tetradec-10-ene-3,5,14-trione

Guidance literature:

Multi-step reaction with 10 steps

1: tetramethylammonium borohydride; acetic acid / acetonitrile / 15 h / -25 °C

2: 759 mg / trifluoroacetic acid / CH₂Cl₂ / 15 h / 20 °C

3: 80 percent / triethylamine; (dimethylamino)pyridine / CH₂Cl₂ / 0.5 h

4: tetrahydrofuran / 0.5 h / -78 °C

5: thionyl chloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 30 h

6: 777 mg / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h

7: 64 percent / MgBr₂*Et₂O; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

8: 71 percent / lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9: 42 percent / triethylamine / toluene / 15 h / 170 °C

10: 99 percent / HCl / tetrahydrofuran / 0.5 h / 20 °C

With hydrogenchloride; dmap; thionyl chloride; tetramethylammonium borohydride; lutidine; tetrabutyl ammonium fluoride; acetic acid; triethylamine; trifluoroacetic acid; magnesium bromide; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 7: Diels-Alder reaction;

DOI:10.1021/jo051318i

upstream raw materials:

acetoacetic acid methyl ester

6-(tert-butyl(diphenyl)silanyloxy)-hex-2-enal