(1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one

Base Information

• Chemical Name: (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one
• CAS No.: 864915-16-2
• Molecular Formula: C₃₂H₄₄O₅Si
• Molecular Weight: 536.784
• Mol file: 864915-16-2.mol

Synonyms:(1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one

Chemical Property of (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one

There total 14 articles about (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one 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: 80.0%

(1R,5S)-7,7-Dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one (864914-92-1) + (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-4-methyl-hex-3-enal (864914-93-2) → (1R,4S,5S)-4-[(E)-(1R,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one + (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one (864915-16-2)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tetlet.2005.06.133

Reference yield:

(2R)-N-[3,3-dimethyl-4,4-bis(trimethylsilyloxy)cyclobutanecarbonyl]-bornane-10,2-sultam (864914-95-4) → (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one (864915-16-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 38 percent / LiAlH₄ / diethyl ether / Heating

2: 94 percent / Et₃N; DMAP / CH₂Cl₂

3: 95 percent / PPTS / CH₂Cl₂

4: 98 percent / dimethylsulfoxide / 70 °C

5: 90 percent / aq. HCl / tetrahydrofuran / 80 °C

6: 80 percent / NaHMDS / tetrahydrofuran / -78 °C

With hydrogenchloride; dmap; lithium aluminium tetrahydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.tetlet.2005.06.133

Reference yield:

(2R)-N-[3,3-dimethyl-4,4-bis(trimethylsilyloxy)cyclobut-1-enecarbonyl]-bornane-10,2-sultam (864914-94-3) → (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one (864915-16-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: L-selectride / toluene

1.2: aq. NH₄Cl / toluene / -78 - 20 °C

2.1: 38 percent / LiAlH₄ / diethyl ether / Heating

3.1: 94 percent / Et₃N; DMAP / CH₂Cl₂

4.1: 95 percent / PPTS / CH₂Cl₂

5.1: 98 percent / dimethylsulfoxide / 70 °C

6.1: 90 percent / aq. HCl / tetrahydrofuran / 80 °C

7.1: 80 percent / NaHMDS / tetrahydrofuran / -78 °C

With hydrogenchloride; dmap; lithium aluminium tetrahydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; L-Selectride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/j.tetlet.2005.06.133

upstream raw materials:

(1R,5S)-7,7-Dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one

(E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-4-methyl-hex-3-enal

(1R,4S)-4-hydroxymethyl-2,2-dimethylcyclobutan-1-ol

(1S,4S)-4-hydroxymethyl-2,2-dimethylcyclobutan-1-ol