2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-ethanol

Base Information

• Chemical Name: 2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-ethanol
• CAS No.: 78173-30-5
• Molecular Formula: C₁₇H₂₂OS
• Molecular Weight: 274.427

Synonyms:2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-ethanol

Chemical Property of 2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-ethanol

Chemical Property:

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Technology Process of 2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-ethanol

There total 5 articles about 2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-ethanol 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: 94.0%

((1S,2S,3S,4R,5S)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.02,6]hept-3-yl)-acetaldehyde (78173-29-2) → 2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.02,6]hept-3-yl)-ethanol (78173-30-5)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1016/0040-4039(80)88099-3

Reference yield:

(1S,4R,5S)-5-Bromomethyl-5-methyl-6-methylene-bicyclo[2.2.1]hept-2-ene (78186-10-4) → 2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.02,6]hept-3-yl)-ethanol (78173-30-5)

Guidance literature:

Multi-step reaction with 4 steps

1: hexamethylphosphoric acid triamide / 12 h / 120 °C

2: 85 percent / CH₂Cl₂ / 0 °C

3: 1) (i-Bu)2AlH, benzene, 0 deg C to room temp., 1 h., 2) 10 percent aq. H₂SO₄, 10 deg C, 1 h.

4: 94 percent / LiBH(C₂H₅)3 / tetrahydrofuran / 18 h / Ambient temperature

With lithium triethylborohydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/0040-4039(80)88099-3

Reference yield:

((1R,2S,4S)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-5-en-2-yl)-acetonitrile (77228-95-6,78173-27-0) → 2-((1R,2S,3R,4S,5R)-2,3-Dimethyl-5-phenylsulfanyl-tricyclo[2.2.1.02,6]hept-3-yl)-ethanol (78173-30-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / CH₂Cl₂ / 0 °C

2: 1) (i-Bu)2AlH, benzene, 0 deg C to room temp., 1 h., 2) 10 percent aq. H₂SO₄, 10 deg C, 1 h.

3: 94 percent / LiBH(C₂H₅)3 / tetrahydrofuran / 18 h / Ambient temperature

With lithium triethylborohydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(80)88099-3

upstream raw materials:

((1S,2S,3S,4R,5S)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-acetaldehyde

(1S,4R,5S)-5-Bromomethyl-5-methyl-6-methylene-bicyclo[2.2.1]hept-2-ene

((1R,2S,4S)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-5-en-2-yl)-acetonitrile

((1S,2S,3S,4R,5S)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-acetonitrile

Downstream raw materials:

3-((1R,2S,3R,4S,5R)-5-Benzenesulfonyl-2,3-dimethyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-propionitrile

2-((1R,2S,3R,4S,5R)-5-Benzenesulfonyl-2,3-dimethyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-ethanol

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