Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester
• CAS No.: 95682-60-3
• Molecular Formula: C₂₂H₂₈O₅S
• Molecular Weight: 404.527
• Mol file: 95682-60-3.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

There total 14 articles about Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl 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%

Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9S,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-2-oxo-dodecahydro-naphtho[1,2-b]furan-6-yl ester (76627-95-7,95782-13-1) → Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester (95682-60-3,99297-03-7)

Guidance literature:

With pyridine; thionyl chloride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(01)98812-X

Reference yield:

2-((1R,6R,7S,8S)-7-Hydroxy-1-methyl-2,5-bis-trimethylsilanyloxy-tricyclo[4.4.0.02,5]dec-8-yl)-propionic acid methyl ester → Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester (95682-60-3,99297-03-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) HCl, 2) NaIO₄ aq / 1) MeOH, 1 h, RT; 2) H₂O-MeOH, 30 min, 25 deg C

2: 98 percent / triethylamine / dimethylformamide / 2 h / Ambient temperature

3: 80 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / Ambient temperature

4: 96 percent / TsOH / 24 h / Ambient temperature

5: 93 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

6: 97 percent / Amberlite IR 120 / methanol / 24 h / Ambient temperature

7: O₂ / Pt / H₂O / 24 h / 50 °C

8: 82 percent / pyridine / 120 h / Ambient temperature

9: 94 percent / pyridine, SOCl₂ / tetrahydrofuran / 1 h / 0 °C

With pyridine; hydrogenchloride; sodium periodate; thionyl chloride; Amberlite IR 120; oxygen; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; platinum; In tetrahydrofuran; pyridine; methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)98812-X

Reference yield:

3-methylcyclohexen-2-one (1193-18-6) → Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester (95682-60-3,99297-03-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) LDA, HMPA / 1) THF, -78 deg C: 2) -20 deg C, 2 h

2: hexane / 504 h / Irradiation

3: NaBH₄ / methanol / 1 h / -20 °C

4: 1) HCl, 2) NaIO₄ aq / 1) MeOH, 1 h, RT; 2) H₂O-MeOH, 30 min, 25 deg C

5: 98 percent / triethylamine / dimethylformamide / 2 h / Ambient temperature

6: 80 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / Ambient temperature

7: 96 percent / TsOH / 24 h / Ambient temperature

8: 93 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

9: 97 percent / Amberlite IR 120 / methanol / 24 h / Ambient temperature

10: O₂ / Pt / H₂O / 24 h / 50 °C

11: 82 percent / pyridine / 120 h / Ambient temperature

12: 94 percent / pyridine, SOCl₂ / tetrahydrofuran / 1 h / 0 °C

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; thionyl chloride; Amberlite IR 120; oxygen; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; platinum; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)98812-X

upstream raw materials:

Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9S,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-2-oxo-dodecahydro-naphtho[1,2-b]furan-6-yl ester

3-methylcyclohexen-2-one

6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone

(R)-2-((1R,2R,4aS,8aR)-4a-Methyl-5,8-dioxo-1-trimethylsilanyloxy-decahydro-naphthalen-2-yl)-propionic acid methyl ester

Downstream raw materials:

α-Santonin

Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Refernces