(E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester

Base Information

• Chemical Name: (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester
• CAS No.: 116386-66-4
• Molecular Formula: C₅₁H₇₈O₇Si₂
• Molecular Weight: 859.347
• Mol file: 116386-66-4.mol

Synonyms:(E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester

Chemical Property of (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester

There total 12 articles about (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl 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: 60.0%

(E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal (116386-65-3) + (S)-2-acetoxy-1,1,2-triphenylethanol (95061-51-1) → (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester (116386-66-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)80074-X

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester (116386-66-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: toluene

3: 2,6-di-t-butyl-4-methyl pyridine / CH₂Cl₂ / 24 h / 22 - 24 °C

4: (iBu)2AlH / tetrahydrofuran / 1 h / -75 °C

5: 78 percent / tetrahydrofuran / -78 - -10 °C

6: n-Bu₂BOTf, diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

8: 60 percent / LDA / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)80074-X

Reference yield:

Imidazole-1-carbothioic acid O-((1R,2S,6R,8R)-9-oxo-4-thioxo-3,5,10-trioxa-tricyclo[6.2.1.02,6]undec-8-yl) ester (116409-60-0) → (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester (116386-66-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) Bu₃SnH; 2.) Bu₃SnH / 2.) AIBN / 1.) xylenes, 140 deg C, 45 min; 2.) xylenes, 140 deg C, 1 h

2: 2,6-lutidine / CH₂Cl₂ / 0 °C

3: toluene

4: 2,6-di-t-butyl-4-methyl pyridine / CH₂Cl₂ / 24 h / 22 - 24 °C

5: (iBu)2AlH / tetrahydrofuran / 1 h / -75 °C

6: 78 percent / tetrahydrofuran / -78 - -10 °C

7: n-Bu₂BOTf, diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

9: 60 percent / LDA / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; di-n-butylboryl trifluoromethanesulfonate; tri-n-butyl-tin hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)80074-X

upstream raw materials:

(E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal

(S)-2-acetoxy-1,1,2-triphenylethanol

triisopropylsilyl trifluoromethanesulfonate

(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexanecarboxaldehyde

Downstream raw materials:

(E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enal