methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate

Base Information

• Chemical Name: methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate
• CAS No.: 758719-48-1
• Molecular Formula: C₂₅H₃₂O₃Si
• Molecular Weight: 408.613

Synonyms:methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate

Chemical Property of methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate

There total 13 articles about methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate 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: 74.0%

(1R,3R,4S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-methanesulfonyloxy-4-methyl-cyclohexanecarboxylic acid methyl ester (758719-56-1) → methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate (758719-48-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at 45 - 50 ℃; for 0.5h;

DOI:10.1002/ejoc.200500289

Reference yield:

(1R,5R)-5-Hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester (757240-15-6) → methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate (758719-48-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1.68 g / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

2.1: BH₃ / tetrahydrofuran / 2.5 h / 0 °C

2.2: 35 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

3.1: 81 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / 20 °C

4.1: 95 percent / K₂CO₃ / methanol / 6 h / 20 °C

5.1: 94 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

6.1: 71 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 45 - 50 °C

With 1H-imidazole; dmap; di-isopropyl azodicarboxylate; borane; potassium tert-butylate; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Mitsunobu inversion;

DOI:10.1002/ejoc.200500289

Reference yield:

(4R,6R)-6-acetoxy-1-methyl-4-(methoxycarbonyl)cyclohexene (326622-28-0) → methyl (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate (758719-48-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: K₂CO₃ / methanol / 6 h

2.1: 1.68 g / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

3.1: BH₃ / tetrahydrofuran / 2.5 h / 0 °C

3.2: 35 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

4.1: 81 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / 20 °C

5.1: 95 percent / K₂CO₃ / methanol / 6 h / 20 °C

6.1: 94 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

7.1: 71 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 45 - 50 °C

With 1H-imidazole; dmap; di-isopropyl azodicarboxylate; borane; potassium tert-butylate; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Mitsunobu inversion;

DOI:10.1002/ejoc.200500289

upstream raw materials:

(1R,3R,4S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-methanesulfonyloxy-4-methyl-cyclohexanecarboxylic acid methyl ester

(1R,5R)-4-methyl-6-oxabicyclo[3.2.1]oct-3-en-7-one

(1R,5R)-5-Hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester

(1R,3R,4S,5R)-4-methyl-6-oxabicyclo[3.2.1]oct-7-one

Downstream raw materials:

(1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

(1R,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methyl-cyclohexanol

(1R,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-2-methyl-cyclohexanol

1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

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