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

Base Information

• Chemical Name: ((1S,2S,3S,4R,5S)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-acetaldehyde
• CAS No.: 78173-29-2
• Molecular Formula: C₁₇H₁₉ClOS
• Molecular Weight: 306.856

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

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

Chemical Property:

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

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

C24H28O6S2 (63025-84-3,78173-26-9) → ((1S,2S,3S,4R,5S)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.02,6]hept-3-yl)-acetaldehyde (78173-29-2)

Guidance literature:

Multi-step reaction with 4 steps

1: LiBr / hexamethylphosphoric acid triamide / 4 h / 120 °C

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

3: 85 percent / CH₂Cl₂ / 0 °C

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

With lithium bromide; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

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

Guidance literature:

Multi-step reaction with 3 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.

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

Guidance literature:

Multi-step reaction with 2 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.

In 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)-acetonitrile

(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

C₂₄H₂₈O₆S₂

Downstream raw materials:

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

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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