3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester

Base Information

Chemical Name:3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester
CAS No.:534600-69-6
Molecular Formula:C₄₇H₅₄O₅S
Molecular Weight:731.009
Hs Code.:

3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester

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Chemical Property of 3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester

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Technology Process of 3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester

There total 18 articles about 3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl 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:

: 1138-41-6
4-hydroxy-3-prenylbenzoic acid

: 534600-69-6
3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 7.5 g / K₂CO₃ / dimethylformamide / 15 h / 20 °C

2.1: SeO₂; tBuO₂H / CH₂Cl₂ / 71 h / 20 °C

2.2: 45 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.5 h / 0 - 20 °C

3.1: 87 percent / Ms₂O; LiBr; collidine / DMAP / dimethylformamide / 24 h / 0 °C

4.1: 1.71 g / nBuLi; HMPA / hexane; tetrahydrofuran / 2.5 h / -65 °C

With 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; selenium(IV) oxide; potassium carbonate; lithium bromide; Methanesulfonic anhydride; dmap; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200390128

Reference yield:

: 100-39-0
benzyl bromide

: 534600-69-6
3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 7.5 g / K₂CO₃ / dimethylformamide / 15 h / 20 °C

2.1: SeO₂; tBuO₂H / CH₂Cl₂ / 71 h / 20 °C

2.2: 45 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.5 h / 0 - 20 °C

3.1: 87 percent / Ms₂O; LiBr; collidine / DMAP / dimethylformamide / 24 h / 0 °C

4.1: 1.71 g / nBuLi; HMPA / hexane; tetrahydrofuran / 2.5 h / -65 °C

With 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; selenium(IV) oxide; potassium carbonate; lithium bromide; Methanesulfonic anhydride; dmap; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200390128

Reference yield:

: 172788-55-5
Methyl <(S)-5-(benzyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3-oxopentanoate

: 534600-69-6
3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: SnCl₄ / CH₂Cl₂

2.1: 76 percent / TMSOTf / CH₂Cl₂ / 20 h / -78 - 0 °C

3.1: 80 percent / H₂ / Pd/C / ethyl acetate / 11 h / 20 °C

4.1: 90 percent / trifluoromethanesulfonyl chloride; DMAP / CH₂Cl₂ / 2 h / 20 °C

5.1: 100 percent / H₂ / Pd/C / ethyl acetate / 19 h / 20 °C

6.1: 91 percent / aq. HCl / tetrahydrofuran / 24 h / 20 °C

7.1: NaH / tetrahydrofuran / 1 h / Heating

7.2: 89 percent / NaH / tetrahydrofuran / 2 h / 20 °C

8.1: CuI / diethyl ether / 1 h / -20 °C

8.2: 87 percent / diethyl ether / 6 h / -10 °C

9.1: 95 percent / DIBAL / hexane; CH₂Cl₂ / 2 h / -65 °C

10.1: MsCl; collidine; LiCl / dimethylformamide / 46 h / 5 °C

11.1: 2.3 g / dimethylformamide / 48 h / 20 °C

12.1: 1.71 g / nBuLi; HMPA / hexane; tetrahydrofuran / 2.5 h / -65 °C

With 2,3,5-trimethyl-pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; copper(l) iodide; n-butyllithium; trifluoromethane sulfonyl chloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200390128