Benzoic acid, 2,4,6-trimethyl-, (3R,5S,6E)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-methoxy-3-methyl- 8-oxo-6-octenyl ester

Base Information

• Chemical Name: Benzoic acid, 2,4,6-trimethyl-, (3R,5S,6E)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-methoxy-3-methyl- 8-oxo-6-octenyl ester
• CAS No.: 850835-64-2
• Molecular Formula: C36H46O5Si
• Molecular Weight: 586.844
• Mol file: 850835-64-2.mol

Synonyms:

Chemical Property of Benzoic acid, 2,4,6-trimethyl-, (3R,5S,6E)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-methoxy-3-methyl- 8-oxo-6-octenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid, 2,4,6-trimethyl-, (3R,5S,6E)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-methoxy-3-methyl- 8-oxo-6-octenyl ester

There total 1 articles about Benzoic acid, 2,4,6-trimethyl-, (3R,5S,6E)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-methoxy-3-methyl- 8-oxo-6-octenyl 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: 97.0%

(E,3R,5S)-7-(methoxycarbonyl)-5-hydroxy-3-methylhept-6-enyl 2,4,6-trimethylbenzoate (850835-63-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (E,3R,5S)-7-(methoxycarbonyl)-5-(tert-butyldiphenylsilanyloxy)-3-methylhept-6-enyl 2,4,6-trimethylbenzoate (850835-64-2)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 12h;

DOI:10.1021/ja050064f

Reference yield: 96.0%

(E,3R,5S)-7-(methoxycarbonyl)-5-(tert-butyldiphenylsilanyloxy)-3-methylhept-6-enyl 2,4,6-trimethylbenzoate (850835-64-2) → (E,4S,6R)-6-methyl-4-(tert-butyldiphenylsilanyloxy)oct-2-ene-1,8-diol

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃; for 0.5h;

DOI:10.1021/ja050064f

Reference yield:

(E,3R,5S)-7-(methoxycarbonyl)-5-(tert-butyldiphenylsilanyloxy)-3-methylhept-6-enyl 2,4,6-trimethylbenzoate (850835-64-2) → (1S,4aR,5S,7S,7aR)-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-1-yl acetate (850835-67-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 96 percent / diisobutylaluminum hydride / hexane; diethyl ether / 0.5 h / -78 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h

3.1: L-proline / dimethylsulfoxide / 5 h / 40 °C

3.2: 910 mg / pyridine; DMAP / dimethylsulfoxide / 0.25 h / 0 °C

With diisobutylaluminium hydride; Dess-Martin periodane; L-proline; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 3.1: intramolecular Michael addition;

DOI:10.1021/ja050064f

upstream raw materials:

(E,3R,5S)-7-(methoxycarbonyl)-5-hydroxy-3-methylhept-6-enyl 2,4,6-trimethylbenzoate

tert-butylchlorodiphenylsilane

Downstream raw materials:

(1S,4aR,5S,7S,7aR)-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-1-yl acetate

(1S,4aS,5S,7S,7aR)-4-formyl-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-1-yl acetate

(1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid

(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester