(3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone

Base Information

Chemical Name:(3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone
CAS No.:171201-49-3
Molecular Formula:C₁₉H₂₄O₅S
Molecular Weight:364.463
Hs Code.:

Synonyms:(3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone

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Chemical Property of (3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone

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Technology Process of (3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone

There total 17 articles about (3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-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: 90.0%

: 98-59-9
p-toluenesulfonyl chloride

: 171201-48-2
(3R,3aR,5R,7aR)-5-hydroxy-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone

: 171201-49-3
(3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 35h;
DOI:10.1021/jo010527+

Reference yield:

: 171201-45-9
(3aR,5R,7aR)-5-hydroxy-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone

: 171201-49-3
(3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / imidazole / dimethylformamide / 20 °C

2.1: LDA; HMPA / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 85 percent / tetrahydrofuran; hexane / 0.5 h

3.1: 85 percent / Bu₄NF*H₂O / tetrahydrofuran / 0.5 h / 20 °C

4.1: 90 percent / pyridine; DMAP / CH₂Cl₂ / 35 h / 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo010527+

Reference yield:

: 204526-19-2
(+)-(1R,5R)-5-Isopropenyl-2-methylcyclohex-2-enylacetic acid

: 171201-49-3
(3R,3aR,5R,7aR)-5-(p-toluenesulfonyloxy)-7a-methyl-3-(2-propenyl)-3a,4,567,7a-hexahydro-2(3H)-benzofuranone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / N-hydroxysuccinimide; DCC / CH₂Cl₂ / 1 h / 20 °C

2.1: 100 percent / imidazole / dimethylformamide / 20 °C

3.1: LDA; HMPA / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 85 percent / tetrahydrofuran; hexane / 0.5 h

4.1: 85 percent / Bu₄NF*H₂O / tetrahydrofuran / 0.5 h / 20 °C

5.1: 90 percent / pyridine; DMAP / CH₂Cl₂ / 35 h / 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 1-hydroxy-pyrrolidine-2,5-dione; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo010527+