(2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

Base Information

Chemical Name:(2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman
CAS No.:1323994-67-7
Molecular Formula:C₂₇H₃₀O₃S
Molecular Weight:434.599
Hs Code.:

Synonyms:(2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

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Chemical Property of (2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

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Technology Process of (2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

There total 4 articles about (2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman 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: 46.0%

: 1323994-24-6
(R(S))-6-(benzyloxy)-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman-2-ol

: 1323994-67-7
(2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

: 1323994-69-9
(2R,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

Guidance literature:: With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 4h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/ejoc.201100436

Reference yield:

: 700-13-0
Trimethylhydroquinone

: 1323994-67-7
(2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

: 1323994-69-9
(2R,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

Guidance literature:: Multi-step reaction with 4 steps

1.1: amberlyst 15 / toluene / Inert atmosphere; Reflux

2.1: potassium carbonate / acetone / Inert atmosphere

2.2: 15 h / Inert atmosphere

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - -40 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 4 h / 0 °C / Inert atmosphere

With triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene;
DOI:10.1002/ejoc.201100436

Reference yield:

: 1323994-23-5
6-(benzyloxy)-5,7,8-trimethylchroman-2-one

: 1323994-67-7
(2S,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

: 1323994-69-9
(2R,R(S))-6-benzyloxy-5,7,8-trimethyl-2-[(p-tolylsulfinyl)methyl]-chroman

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - -40 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 4 h / 0 °C / Inert atmosphere

With triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/ejoc.201100436