[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Base Information

• Chemical Name: [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester
• CAS No.: 198193-33-8
• Molecular Formula: C₅₈H₉₈O₈Si₃
• Molecular Weight: 1007.67
• Mol file: 198193-33-8.mol

Synonyms:[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Chemical Property of [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-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-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

There total 26 articles about [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-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: 94.0%

[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((E)-(3S,4R)-1,3,5,5-tetramethyl-6-oxo-4-triethylsilanyloxy-hex-1-enyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (172268-36-9) + C16H31LiOSi → [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (198193-33-8)

Guidance literature:

With magnesium bromide; In tetrahydrofuran; diethyl ether; pentane; benzene; at -78 ℃; for 1h;

DOI:10.1021/ja972497r

Reference yield:

(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde (172587-76-7) → [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (198193-33-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 96 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

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

3: 80 percent / magnesium chloride / tetrahydrofuran; diethyl ether / 1.) reflux 20 min, 2.) -78 deg C, 1.5 h

4: 95 percent / H₂, quinoline / 5percent palladium on calcium carbonate / hexane / 1.5 h

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

6: 74 percent / p-toluenesulfonic acid / dimethylformamide; H₂O / 24 h / Heating

7: 90 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.67 h / 0 °C

8: 96 percent / silver carbonate on Celite / benzene / 19 h / Heating

9: 87 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

10: 94 percent / citric acid / 1.5 h / Heating

11: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.67 h / Ambient temperature

12: 62 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

13: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

14: 88 percent / triethylsilane / 10percent Pd on carbon / CH₂Cl₂ / 2 h / Ambient temperature

15: 94 percent / magnesium bromide / tetrahydrofuran; diethyl ether; benzene; pentane / 1 h / -78 °C

With pyridine; 2,6-dimethylpyridine; quinoline; triethylsilane; dmap; n-butyllithium; 18-crown-6 ether; hydrogen; potassium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; silver carbonate; trifluoroacetic acid; citric acid; magnesium bromide; magnesium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; pentane; benzene;

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-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (198193-33-8)

Guidance literature:

Multi-step reaction with 14 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

9: 94 percent / citric acid / 1.5 h / Heating

10: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.67 h / Ambient temperature

11: 62 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

12: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

13: 88 percent / triethylsilane / 10percent Pd on carbon / CH₂Cl₂ / 2 h / Ambient temperature

14: 94 percent / magnesium bromide / tetrahydrofuran; diethyl ether; benzene; pentane / 1 h / -78 °C

With pyridine; 2,6-dimethylpyridine; quinoline; triethylsilane; dmap; n-butyllithium; 18-crown-6 ether; hydrogen; potassium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; silver carbonate; trifluoroacetic acid; citric acid; magnesium bromide; magnesium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; pentane; benzene;

DOI:10.1021/ja972497r

upstream raw materials:

[(E)-(R)-1-((E)-3-Bromo-but-2-enyl)-hex-4-enyloxy]-triethyl-silane

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

ethyl β-methylthiopropionate

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

Downstream raw materials:

(7E,13E)-(1R,5R,9R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-1,9-dihydroxy-8,10,10,12,14-pentamethyl-5-((E)-pent-3-enyl)-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-diene-3,11-dione

(1Z,7E,13E)-(5R,9R,11R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-9,11-dihydroxy-8,10,10,12,14-pentamethyl-5-((E)-pent-3-enyl)-4,19-dioxa-bicyclo[13.3.1]nonadeca-1,7,13-trien-3-one

(7E,13E)-(1R,5R,9R,11R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-9,11-dihydroxy-1-methoxy-8,10,10,12,14-pentamethyl-5-((E)-pent-3-enyl)-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-dien-3-one

[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E,13E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7,13-trienyl)-tetrahydro-pyran-2-yl]-acetic acid