(1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol

Base Information

Chemical Name:(1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol
CAS No.:671798-74-6
Molecular Formula:C₂₉H₄₈O₃SSi₂
Molecular Weight:532.935
Hs Code.:

Synonyms:(1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol

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Chemical Property of (1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol

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Technology Process of (1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol

There total 1 articles about (1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol 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:

: 187803-40-3
3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde

: 671798-74-6
(1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: (4R,trans)-2,2-Me₂-tetraphenyl-1,3-dioxolane-4,5-dimethanol; CpTiCl₃ / tetrahydrofuran; diethyl ether / 3.5 h / -78 - 0 °C

1.2: 98 percent / tetrahydrofuran; diethyl ether / 2 h / -78 °C

2.1: 85 percent / AIBN / 10 h / 80 °C

With cyclopentadienyl titanium(IV) trichloride; 2,2'-azobis(isobutyronitrile); (S,S)-taddol; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ol036339i

Reference yield: 56.0%

: 671798-86-0
(3S,5S,6R)-6-[2-(4-methoxyphenoxy)ethyl]-3,5-dimethyltetrahydropyran-2-one

: 671798-74-6
(1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol

: 671798-94-0
(2R,3S,5S,6R,8S,9S)-8-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-[2-(4-methoxyphenoxy)ethyl]-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecane

Guidance literature:: (1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol; With n-butyllithium; lithium 4,4′-di(tert-butyl)biphenyl; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

With magnesium bromide; In tetrahydrofuran; hexane; at -78 - -42 ℃; for 0.5h;

(3S,5S,6R)-6-[2-(4-methoxyphenoxy)ethyl]-3,5-dimethyltetrahydropyran-2-one; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.5h;
DOI:10.1021/ol036339i

Reference yield:

: 671798-74-6
(1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol

: 5-{(2S,3S,6R,8R,9S,11S)-8-[2-(4-methoxyphenoxy)ethyl]-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undec-2-yl}benzene-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: n- BuLi; LiDBB / tetrahydrofuran; hexane / 0.75 h / -78 °C

1.2: MgBr₂ / tetrahydrofuran; hexane / 0.5 h / -78 - -42 °C

1.3: 56 percent / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C

2.1: 66 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

With n-butyllithium; lithium 4,4′-di(tert-butyl)biphenyl; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane;
DOI:10.1021/ol036339i