[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Base Information

• Chemical Name: [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester
• CAS No.: 172268-63-2
• Molecular Formula: C₃₇H₅₈O₆Si₂
• Molecular Weight: 655.035
• Mol file: 172268-63-2.mol

Synonyms:[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Chemical Property of [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

There total 12 articles about [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid 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: 87.0%

ethyl acetate (141-78-6) + (4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-tetrahydro-pyran-2-one (172268-41-6) → [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (172268-63-2)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/ja972497r

Reference yield:

1-[(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-but-2-yn-1-ol → [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (172268-63-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 83 percent / dicyclohexylcarbodiimide, dimethyl sulfoxide, trifluoroacetic acid, pyridine / benzene / 2 h / Ambient temperature

2: 80 percent / magnesium chloride / tetrahydrofuran; diethyl ether / 1.) reflux 20 min, 2.) -78 deg C, 1.5 h

3: 95 percent / H₂, quinoline / 5percent palladium on calcium carbonate / hexane / 1.5 h

4: 1.) potassium hydride, 18-crown-6, 2.) n-butyllithium / 1.) THF, room temperature, 45 min, 2.) THF, hexane, -78 deg C, 1.5 h

5: 74 percent / p-toluenesulfonic acid / dimethylformamide; H₂O / 24 h / Heating

6: 90 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.67 h / 0 °C

7: 96 percent / silver carbonate on Celite / benzene / 19 h / Heating

8: 87 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

With pyridine; quinoline; dmap; n-butyllithium; 18-crown-6 ether; hydrogen; potassium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; silver carbonate; trifluoroacetic acid; magnesium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja972497r

Reference yield:

(R)-2-[(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol (172268-60-9) → [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (172268-63-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / H₂, quinoline / 5percent palladium on calcium carbonate / hexane / 1.5 h

2: 1.) potassium hydride, 18-crown-6, 2.) n-butyllithium / 1.) THF, room temperature, 45 min, 2.) THF, hexane, -78 deg C, 1.5 h

3: 74 percent / p-toluenesulfonic acid / dimethylformamide; H₂O / 24 h / Heating

4: 90 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.67 h / 0 °C

5: 96 percent / silver carbonate on Celite / benzene / 19 h / Heating

6: 87 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

With quinoline; dmap; n-butyllithium; 18-crown-6 ether; hydrogen; potassium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; silver carbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja972497r

upstream raw materials:

ethyl acetate

(4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-tetrahydro-pyran-2-one

(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

(R)-2-[(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol

Downstream raw materials:

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(1S,2S)-4-[(2S,4S,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-ethoxycarbonylmethyl-6-methoxy-tetrahydro-pyran-2-yl]-1-(1-ethylsulfanylcarbonyl-1-methyl-ethyl)-2-methyl-pent-3-enyl ester

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(1S,2S)-4-[(2S,4S,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-ethoxycarbonylmethyl-6-methoxy-tetrahydro-pyran-2-yl]-1-(1-ethylsulfanylcarbonyl-1-methyl-ethyl)-2-methyl-pent-3-enyl ester

[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(3S,4R)-5-ethylsulfanylcarbonyl-4-hydroxy-1,3,5-trimethyl-hex-1-enyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(3S,4S)-5-ethylsulfanylcarbonyl-4-hydroxy-1,3,5-trimethyl-hex-1-enyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester