(3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone

Base Information

• Chemical Name: (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone
• CAS No.: 204526-17-0
• Molecular Formula: C₁₇H₂₂O₅S
• Molecular Weight: 338.425
• Mol file: 204526-17-0.mol

Synonyms:

Chemical Property of (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone

There total 10 articles about (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone 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: 79.0%

p-toluenesulfonyl chloride (98-59-9) + (3R,3aR,5R,7aR)-5-hydroxy-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone (204526-30-7) → (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone (204526-17-0)

Guidance literature:

With pyridine; dmap; In dichloromethane; Ambient temperature;

DOI:10.1016/S0957-4166(97)00641-1

Reference yield:

(+)-trans-carveol (2102-58-1,22567-18-6,20307-86-2) → (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone (204526-17-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) propionic acid, 2.) aq. KOH / 1.) 100-135 deg C, 17 h, 2.) MeOH, reflux, 2 h

2: 86 percent / NBS / acetone / 0.5 h / Ambient temperature

3: 95 percent / n-Bu₃SnH, AIBN / tetrahydrofuran / 1.5 h / 60 °C

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂,20 deg C, 15 h

5: 87 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 48 h / Ambient temperature

6: 74 percent / MeONa, MeOH / 0.75 h

7: 100 percent / imidazole / dimethylformamide / 1 h

8: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, RT, 4 h

9: 98 percent / Bu₄NF*H₂O / tetrahydrofuran / 0.5 h / Ambient temperature

10: 79 percent / pyridine, DMAP / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium hydroxide; N-Bromosuccinimide; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; sodium hydrogencarbonate; ozone; propionic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0957-4166(97)00641-1

Reference yield:

(3aR,5R,7aR)-5-hydroxy-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone (171201-45-9) → (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone (204526-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / imidazole / dimethylformamide / 1 h

2: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, RT, 4 h

3: 98 percent / Bu₄NF*H₂O / tetrahydrofuran / 0.5 h / Ambient temperature

4: 79 percent / pyridine, DMAP / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(97)00641-1

upstream raw materials:

p-toluenesulfonyl chloride

(3R,3aR,5R,7aR)-5-hydroxy-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone

(+)-trans-carveol

(3aR,5R,7aR)-5-hydroxy-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone