(+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

Base Information

Chemical Name:(+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate
CAS No.:674781-59-0
Molecular Formula:C₂₃H₃₁BrO₅S
Molecular Weight:499.466
Hs Code.:

Synonyms:(+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

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Chemical Property of (+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

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Technology Process of (+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

There total 8 articles about (+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate 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: 97.0%

: 674781-57-8
(+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfanyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

: 674781-59-0
(+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/ol0363063

Reference yield:

: 166022-29-3
(S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol

: 674781-59-0
(+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

Guidance literature:: Multi-step reaction with 7 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: Mg / tetrahydrofuran

2.2: tetrahydrofuran / 0.5 h / 0 °C

2.3: 2.5 g / HMPA / tetrahydrofuran / 0 - 20 °C

3.1: 57 percent / PPh₃; AcOH / Pd(OAc)2 / 760 Torr / Heating

4.1: 92 percent / K₂CO₃ / acetone / 4 h / 20 °C

5.1: 78 percent / aq. NaOH; benzyltriethylammonium chloride; MeOH / CH₂Cl₂ / 8 h / 20 °C

6.1: 99 percent / 1,1,1,3,3,3-hexafluoro-2-propanol; NaHCO₃ / 4 h / 20 °C

7.1: 97 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

With methanol; sodium hydroxide; oxalyl dichloride; 1,1,1,3',3',3'-hexafluoro-propanol; N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; potassium carbonate; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium diacetate; In tetrahydrofuran; dichloromethane; acetone; 1.1: Swern oxidation;
DOI:10.1021/ol0363063

Reference yield:

: 166022-30-6
(S)-(+)-2',2'-dimethyl-6'-methylene-1'-cyclohexylcarboxaldehyde

: 674781-59-0
(+)-methyl [(4aS,8R,8aS)-7-bromo-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: Mg / tetrahydrofuran

1.2: tetrahydrofuran / 0.5 h / 0 °C

1.3: 2.5 g / HMPA / tetrahydrofuran / 0 - 20 °C

2.1: 57 percent / PPh₃; AcOH / Pd(OAc)2 / 760 Torr / Heating

3.1: 92 percent / K₂CO₃ / acetone / 4 h / 20 °C

4.1: 78 percent / aq. NaOH; benzyltriethylammonium chloride; MeOH / CH₂Cl₂ / 8 h / 20 °C

5.1: 99 percent / 1,1,1,3,3,3-hexafluoro-2-propanol; NaHCO₃ / 4 h / 20 °C

6.1: 97 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

With methanol; sodium hydroxide; 1,1,1,3',3',3'-hexafluoro-propanol; N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; potassium carbonate; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium diacetate; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1021/ol0363063