(1R,2S,R_S)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol

Base Information

• Chemical Name: (1R,2S,R_S)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol
• CAS No.: 213747-11-6
• Molecular Formula: C₂₇H₃₃ClO₃SSi
• Molecular Weight: 501.162

Synonyms:(1R,2S,R_S)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol

Chemical Property of (1R,2S,R_S)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol

Chemical Property:

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Technology Process of (1R,2S,R_S)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol

There total 1 articles about (1R,2S,R_S)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol 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: 38.0%

(R)-chloromethyl p-tolyl sulfoxide (31350-91-1) + 1-(tert-butyldiphenylsilyloxy)-2-propanone (118171-02-1) → (1R,2S,RS)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol (213747-11-6) + (1R,2R,RS)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo980320p

Reference yield: 99.0%

(1R,2S,RS)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol (213747-11-6) → (2S,3R,RS)-2-(tert-butyldiphenylsilanyloxy)methyl-2-methyl-3-(p-tolylsulfinyl)oxirane

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at 0 ℃;

DOI:10.1016/j.tet.2006.06.112

Reference yield:

(1R,2S,RS)-(-)-3-(tert-butyldiphenylsilanyloxy)-1-chloro-2-methyl-1-(p-tolylsulfinyl)-2-propanol (213747-11-6) → tert-Butyl-[(2S,3R)-2-methyl-3-(toluene-4-sulfonyl)-oxiranylmethoxy]-diphenyl-silane (189347-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 788 mg / t-BuOK / 2-methyl-propan-2-ol; CH₂Cl₂ / 0.5 h / Ambient temperature

2: 97 percent / m-CPBA / CH₂Cl₂ / 4 h / Ambient temperature

With potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo980320p

upstream raw materials:

(R)-chloromethyl p-tolyl sulfoxide

1-(tert-butyldiphenylsilyloxy)-2-propanone

Downstream raw materials:

methyl (R)-(-)-2-azido-3-(tert-butyldiphenylsilanyloxy)-2-methylpropionate

tert-Butyl-[(2S,3R)-2-methyl-3-(toluene-4-sulfonyl)-oxiranylmethoxy]-diphenyl-silane

(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

(2R,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-hexahydro-pyrano[3,2-b]pyran-3-one

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