(+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone

Base Information

• Chemical Name: (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone
• CAS No.: 210964-88-8
• Molecular Formula: C₂₈H₃₆Cl₂O₂
• Molecular Weight: 475.499

Synonyms:(+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone

Chemical Property of (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone

Chemical Property:

Purity/Quality:

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Technology Process of (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone

There total 4 articles about (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone 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: 69.0%

trifluoroacetyl chloride (76-02-8) + (-)-2-{(1R)-1-[((1Z)-3-phenyl-1-propenyl)oxy]ethyl}-1,3,5-triisopropylbenzene (210964-87-7) → (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone (210964-88-8)

Guidance literature:

With copper; zinc; In diethyl ether; for 2.5h;

DOI:10.1021/jo9801162

Reference yield:

benzyl bromide (100-39-0) → (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone (210964-88-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) KH, 3.) n-BuLi / 1) THF; 2) THF, -50 deg C, 15 min, -50 --> 20 deg C, 1 h; 3) THF, hexane, -70 deg C, 30 min, -70 to -40 deg C, 30 min; 4) THF, hexane, hexamethylphosphoramide, 20 deg C, 2 h

2: H₂ / Pd-BaSO₄ / pyridine / 5 h

3: 69 percent / Zn-Cu couple / diethyl ether / 2.5 h

With n-butyllithium; hydrogen; potassium hydride; copper; zinc; palladium on barium sulfate; In pyridine; diethyl ether;

DOI:10.1021/jo9801162

Reference yield:

(R)-(+)-1-(2,4,6-triisopropylphenyl)ethanol (181531-14-6) → (+)-(2S,3R)-2-benzyl-4,4-dichloro-3-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]cyclobutanone (210964-88-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) KH, 3.) n-BuLi / 1) THF; 2) THF, -50 deg C, 15 min, -50 --> 20 deg C, 1 h; 3) THF, hexane, -70 deg C, 30 min, -70 to -40 deg C, 30 min; 4) THF, hexane, hexamethylphosphoramide, 20 deg C, 2 h

2: H₂ / Pd-BaSO₄ / pyridine / 5 h

3: 69 percent / Zn-Cu couple / diethyl ether / 2.5 h

With n-butyllithium; hydrogen; potassium hydride; copper; zinc; palladium on barium sulfate; In pyridine; diethyl ether;

DOI:10.1021/jo9801162

upstream raw materials:

trifluoroacetyl chloride

(-)-2-{(1R)-1-[((1Z)-3-phenyl-1-propenyl)oxy]ethyl}-1,3,5-triisopropylbenzene

benzyl bromide

(R)-(+)-1-(2,4,6-triisopropylphenyl)ethanol

Downstream raw materials:

(4R,5S)-5-benzyl-3,3-dichloro-4-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]-2-pyrrolidinone

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