(+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane

Base Information

• Chemical Name: (+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane
• CAS No.: 435286-51-4
• Molecular Formula: C₁₆H₂₀O₄S
• Molecular Weight: 308.398

Synonyms:(+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane

Chemical Property of (+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane

Chemical Property:

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Technology Process of (+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane

There total 13 articles about (+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane 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:

(-)-(2S,3Z)-5-benzenesulfonyl-1-iodo-2-(tetrahydropyran-2-yloxy)-pent-3-ene (613682-73-8) → (+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane (435286-51-4) + (-)-(1R,2R)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane (435286-54-7)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/ol035451d

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane (435286-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / p-TsOH / CH₂Cl₂ / 4 h

2: HMDSNa / tetrahydrofuran / 1 h / -78 °C

With sodium hexamethyldisilazane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol035451d

Reference yield:

(+)-(2S)-5-benzenesulfonyl-1-iodo-2-(tetrahydropyran-2-yloxy)-pent-3-ene (435286-48-9) → (+)-(1R,2S)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane (435286-51-4) + (-)-(1R,2R)-2-[2-(2-benzenesulfonylvinyl)-1-(tetrahydropyran-2-yloxy)]-cyclopropane (435286-54-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1055/s-2002-19749 DOI:10.1055/s-2003-36256

upstream raw materials:

(+)-(2S)-5-benzenesulfonyl-1-iodo-2-(tetrahydropyran-2-yloxy)-pent-3-ene

(-)-(2S,3Z)-5-benzenesulfonyl-1-iodo-2-(tetrahydropyran-2-yloxy)-pent-3-ene

3,4-dihydro-2H-pyran

(-)-(4S)-2,2-Dimethyl-4-[(Z)-3-phenylsulfonylprop-1-enyl]-1,3-dioxolane

Downstream raw materials:

(+)-(1R,2S)-2-(2-benzenesulfonylethyl)-1-(tetrahydropyran-2-yloxy)-cyclopropane

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