(2R,4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide

Base Information

• Chemical Name: (2R,4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide
• CAS No.: 405297-44-1
• Molecular Formula: C₁₈H₃₁ClO₃SSi
• Molecular Weight: 391.047

Synonyms:(2R,4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide

Chemical Property of (2R,4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide

Chemical Property:

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Technology Process of (2R,4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide

There total 3 articles about (2R,4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide 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: 84.0%

(4R,RS)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-oxopentyl p-tolyl sulfoxide (405297-43-0) → (2R,4R,RS)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide (405297-44-1)

Guidance literature:

(4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-oxopentyl p-tolyl sulfoxide; With zinc(II) chloride; In tetrahydrofuran; at 20 ℃; for 1.5h;

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; Further stages.;

DOI:10.1021/ja017177t

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,4R,RS)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide (405297-44-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / imidazole / tetrahydrofuran; dimethylformamide / 66 h / 20 °C

2.1: 72 percent / tetrahydrofuran; hexane; diethyl ether / 1.25 h / -60 °C

3.1: ZnCl₂ / tetrahydrofuran / 1.5 h / 20 °C

3.2: 84 percent / DIBAL / tetrahydrofuran; toluene / -78 °C

With 1H-imidazole; zinc(II) chloride; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ja017177t

Reference yield:

ethyl (3R)-4-chloro-3-[(1,1-dimethylethyl)dimethylsilyl]oxybutanoate (199613-61-1) → (2R,4R,RS)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-hydroxypentyl p-tolyl sulfoxide (405297-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 72 percent / tetrahydrofuran; hexane; diethyl ether / 1.25 h / -60 °C

2.1: ZnCl₂ / tetrahydrofuran / 1.5 h / 20 °C

2.2: 84 percent / DIBAL / tetrahydrofuran; toluene / -78 °C

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/ja017177t

upstream raw materials:

(4R,R_S)-5-chloro-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-oxopentyl p-tolyl sulfoxide

tert-butyldimethylsilyl chloride

ethyl (3R)-4-chloro-3-[(1,1-dimethylethyl)dimethylsilyl]oxybutanoate

Downstream raw materials:

(2R,4R,R_S)-4,5-epoxy-2-hydroxypentyl p-tolyl sulfoxide

Benzoic acid (R)-2-benzenesulfonyl-1-((E)-2-{(4R,6S)-6-[(2Z,4E)-6-(tert-butyl-dimethyl-silanyloxy)-hexa-2,4-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-vinyl)-6-triisopropylsilanyloxy-heptyl ester

(2E,4Z,10E,12E)-(7S,9R,17R)-1-[(1,1-dimethylethyl)silyl]oxy-7,9-isopropylidenedioxy-12-(phenylsulfonyl)-17-[tris(1-methylethyl)silyl]oxyoctadeca-2,4,10,12-tetraene

(6Z,8E)-(2R,4S,R_S)-2,4-dihydroxy-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-6,8-decadienyl p-tolyl sulfoxide

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