(1R,2R,3S,6S,R_S)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane

Base Information

• Chemical Name: (1R,2R,3S,6S,R_S)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane
• CAS No.: 139965-09-6
• Molecular Formula: C₂₁H₂₅FO₂S
• Molecular Weight: 360.493

Synonyms:(1R,2R,3S,6S,R_S)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane

Chemical Property of (1R,2R,3S,6S,R_S)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane

Chemical Property:

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Technology Process of (1R,2R,3S,6S,R_S)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane

There total 6 articles about (1R,2R,3S,6S,R_S)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane 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: 85.0%

benzyl bromide (100-39-0) + (1R,2S,5S,6R,RS)-6-fluoro-5-methyl-2-<(4-methylphenyl)sulphinyl>cyclohexan-1-ol (139965-03-0) → (1R,2R,3S,6S,RS)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane (139965-09-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/jo00100a057

Reference yield:

(2S,3S,RS)-1,1-Dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>hept-6-en-2-ol (139965-00-7) → (1R,2R,3S,6S,RS)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane (139965-09-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 33.1 percent / tributyltin hydride, AIBN / benzene / 5 h / 74 °C

2: 40 percent / Bu₃SnH / benzene / 5 h / 74 °C

3: 85 percent / NaH / dimethylformamide / 1 h / 0 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00100a057

Reference yield:

(+)-(RS)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene (118558-73-9) → (1R,2R,3S,6S,RS)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane (139965-09-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / LDA / tetrahydrofuran / 0.08 h / -65 °C

2: 19 percent / NaBH₄ / methanol; aq. NH₃ / 0.17 h / -20 °C

3: 33.1 percent / tributyltin hydride, AIBN / benzene / 5 h / 74 °C

4: 40 percent / Bu₃SnH / benzene / 5 h / 74 °C

5: 85 percent / NaH / dimethylformamide / 1 h / 0 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; ammonium hydroxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00100a057

upstream raw materials:

benzyl bromide

(1R,2S,5S,6R,R_S)-6-fluoro-5-methyl-2-<(4-methylphenyl)sulphinyl>cyclohexan-1-ol

(1S,2R,3S,6S,R_S)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol

(1S,2S,3S,6S,R_S)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol

Downstream raw materials:

(3S,4R,5S)-3-(Benzyloxy)-4-fluoro-5-methylcyclohex-1-ene

(1R,2R,3S,4R,5S)-3-(Benzyloxy)-4-fluoro-5-methylcyclohexane-1,2-diol

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