Toluene-4-sulfonic acid (E)-6-[(1R,2S,3R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-6-[(1R,2S,3R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-enyl ester
• CAS No.: 443796-72-3
• Molecular Formula: C₃₀H₄₉ClO₆SSi
• Molecular Weight: 601.32
• Mol file: 443796-72-3.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (E)-6-[(1R,2S,3R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (E)-6-[(1R,2S,3R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-enyl ester

There total 12 articles about Toluene-4-sulfonic acid (E)-6-[(1R,2S,3R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-enyl 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:

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (65025-95-8) → Toluene-4-sulfonic acid (E)-6-[(1R,2S,3R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-enyl ester (443796-72-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 30.4 g / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

2: 26.3 g / 2,4,6-trimethylpyridine / CH₂Cl₂ / 1 h / -78 °C

3: 100 percent / pyridine / 16 h / 20 °C

4: 78 percent / tetrabutylammonium chloride; potassium carbonate / toluene / 4 h / 50 °C

5: 83 percent / NaOH / methanol; H₂O / 0.5 h / 20 °C

6: 15.5 g / dimethyl sulfoxide; triethylamine; sulfur trioxide-pyridine complex / 1 h / 20 °C

7: 13.4 g / tetrahydrofuran / 1 h / -78 °C

8: 63 percent / propionic acid; triethylamine / 2 h / 140 °C

9: 9.03 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

10: 12.1 g / pyridine / 5 h / 20 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl-ammonium chloride; sulfur trioxide pyridine complex; potassium carbonate; dimethyl sulfoxide; propionic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; 7: Grignard reaction;

DOI:10.1016/S0968-0896(02)00008-1

Reference yield:

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3) → Toluene-4-sulfonic acid (E)-6-[(1R,2S,3R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-enyl ester (443796-72-3)

Guidance literature:

Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 20 °C

2: 30.4 g / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

3: 26.3 g / 2,4,6-trimethylpyridine / CH₂Cl₂ / 1 h / -78 °C

4: 100 percent / pyridine / 16 h / 20 °C

5: 78 percent / tetrabutylammonium chloride; potassium carbonate / toluene / 4 h / 50 °C

6: 83 percent / NaOH / methanol; H₂O / 0.5 h / 20 °C

7: 15.5 g / dimethyl sulfoxide; triethylamine; sulfur trioxide-pyridine complex / 1 h / 20 °C

8: 13.4 g / tetrahydrofuran / 1 h / -78 °C

9: 63 percent / propionic acid; triethylamine / 2 h / 140 °C

10: 9.03 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

11: 12.1 g / pyridine / 5 h / 20 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl-ammonium chloride; sulfur trioxide pyridine complex; potassium carbonate; dimethyl sulfoxide; propionic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 8: Grignard reaction;

DOI:10.1016/S0968-0896(02)00008-1

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Toluene-4-sulfonic acid (E)-6-[(1R,2S,3R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-enyl ester (443796-72-3)

Guidance literature:

Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 20 °C

2: 30.4 g / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

3: 26.3 g / 2,4,6-trimethylpyridine / CH₂Cl₂ / 1 h / -78 °C

4: 100 percent / pyridine / 16 h / 20 °C

5: 78 percent / tetrabutylammonium chloride; potassium carbonate / toluene / 4 h / 50 °C

6: 83 percent / NaOH / methanol; H₂O / 0.5 h / 20 °C

7: 15.5 g / dimethyl sulfoxide; triethylamine; sulfur trioxide-pyridine complex / 1 h / 20 °C

8: 13.4 g / tetrahydrofuran / 1 h / -78 °C

9: 63 percent / propionic acid; triethylamine / 2 h / 140 °C

10: 9.03 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

11: 12.1 g / pyridine / 5 h / 20 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl-ammonium chloride; sulfur trioxide pyridine complex; potassium carbonate; dimethyl sulfoxide; propionic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 8: Grignard reaction;

DOI:10.1016/S0968-0896(02)00008-1

upstream raw materials:

p-toluenesulfonyl chloride

(E)-6-[(1R,2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-chloro-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hex-4-en-1-ol

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one