[(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane
• CAS No.: 152300-64-6
• Molecular Formula: C₄₅H₅₈O₅SSi
• Molecular Weight: 739.104

Synonyms:[(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane

Chemical Property of [(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane

There total 20 articles about [(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane 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: 76.0%

tert-Butyl-[(E)-(1R,2S,5S,6S)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-8-phenylsulfanyl-oct-3-enyloxy]-diphenyl-silane → [(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane (152300-64-6)

Guidance literature:

With ozone; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4039(00)73993-1

Reference yield:

2-methylbut-2-enal (497-03-0) → [(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane (152300-64-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 85 percent / di-n-butylboron triflate, Et₃N / CH₂Cl₂ / -78 deg C up to RT

2: 85 percent / NaOMe / methanol; CH₂Cl₂ / 0.17 h / -15 °C

3: 88 percent / DIBAL-H / CH₂Cl₂ / -78 - -15 °C

4: 82 percent / Bu₃P / dimethylformamide / Ambient temperature

5: 96 percent / imidazole / dimethylformamide / 85 °C

6: 99 percent / O₃ / tetrahydrofuran; methanol; H₂O / Ambient temperature

7: 64 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C up to RT

8: 92 percent / 1.) (CF₃CO)2O/Me₂SO; 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C; 2.) up to RT

9: 82 percent / Bu₃SnH, AIBN / toluene / Heating

10: 63 percent / tetrahydrofuran; dibutyl ether / -78 deg C up to RT

11: POCl₃, pyridine / 14 h / 55 °C

12: 86 percent / HF-pyridine / tetrahydrofuran

13: 98 percent / Bu₃P / tetrahydrofuran

14: 76 percent / O₃ / tetrahydrofuran; methanol; H₂O

With pyridine; 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; tri-n-butyl-tin hydride; sodium methylate; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; trichlorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; dibutyl ether; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)73993-1

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → [(E)-(1R,2S,5S,6S)-8-Benzenesulfonyl-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-1-((E)-1-methyl-propenyl)-oct-3-enyloxy]-tert-butyl-diphenyl-silane (152300-64-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 84 percent / TsOH / dimethylformamide / 55 °C

2: 78 percent / DIBAL-H / CH₂Cl₂; toluene / -78 deg C up to RT

3: 83 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C up to RT

4: 64 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C up to RT

5: 92 percent / 1.) (CF₃CO)2O/Me₂SO; 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C; 2.) up to RT

6: 82 percent / Bu₃SnH, AIBN / toluene / Heating

7: 63 percent / tetrahydrofuran; dibutyl ether / -78 deg C up to RT

8: POCl₃, pyridine / 14 h / 55 °C

9: 86 percent / HF-pyridine / tetrahydrofuran

10: 98 percent / Bu₃P / tetrahydrofuran

11: 76 percent / O₃ / tetrahydrofuran; methanol; H₂O

With pyridine; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; trichlorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; dibutyl ether; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)73993-1

upstream raw materials:

2-methylbut-2-enal

p-Anisaldehyde dimethyl acetal

(2R,3R,4E)-3-hydroxy-2,4-dimethyl-4-hexenoic acid methyl ester

(2S,3R)-(E)-2,4-dimethyl-3-hydroxy-4-hexen-1-ol

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