(-)-(2S,S_S)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide

Base Information

• Chemical Name: (-)-(2S,S_S)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide
• CAS No.: 364049-59-2
• Molecular Formula: C₂₄H₂₃F₂NO₃S
• Molecular Weight: 443.514

Synonyms:(-)-(2S,S_S)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide

Chemical Property of (-)-(2S,S_S)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide

Chemical Property:

Purity/Quality:

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Technology Process of (-)-(2S,S_S)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide

There total 5 articles about (-)-(2S,S_S)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide 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: 76.0%

benzyl chloroformate (501-53-1,94274-21-2) + (S)-2,2-Difluoro-1-((S)-naphthalene-1-sulfinylmethyl)-pent-4-enylamine → (-)-(2S,SS)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide (364049-59-2)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; water; at 20 ℃; for 2h;

DOI:10.1021/ol016087q

Reference yield:

(S)-(-)-methyl 1-naphthyl sulfoxide (63699-45-6) → (-)-(2S,SS)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide (364049-59-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / LDA / tetrahydrofuran / 6 h / -78 - 20 °C

2: Bu₄NBH₄ / methanol; tetrahydrofuran / 5 h / -70 - 20 °C

3: CAN / acetonitrile; H₂O / 0.5 h / 0 °C

4: 76 percent / K₂CO₃ / dioxane; H₂O / 2 h / 20 °C

With ammonium cerium(IV) nitrate; tetrabutylammonium borohydride; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile;

DOI:10.1021/ol016087q

Reference yield:

N-(4-methoxyphenyl)-1-chloro-2,2-difluoro-4-pentenimidoyl chloride (364049-82-1) → (-)-(2S,SS)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexenyl-1-(1-naphtyl)sulfoxide (364049-59-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / LDA / tetrahydrofuran / 6 h / -78 - 20 °C

2: Bu₄NBH₄ / methanol; tetrahydrofuran / 5 h / -70 - 20 °C

3: CAN / acetonitrile; H₂O / 0.5 h / 0 °C

4: 76 percent / K₂CO₃ / dioxane; H₂O / 2 h / 20 °C

With ammonium cerium(IV) nitrate; tetrabutylammonium borohydride; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile;

DOI:10.1021/ol016087q

upstream raw materials:

benzyl chloroformate

(S)-(-)-methyl 1-naphthyl sulfoxide

N-(4-methoxyphenyl)-1-chloro-2,2-difluoro-4-pentenimidoyl chloride

(-)-(2S,S_S)-3,3-difluoro-N-(p-methoxyphenyl)-2-amino-5-hexenyl-1-(1-naphtyl)sulfoxide

Downstream raw materials:

(-)-(2R)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexen-1-ol

(-)-(1R)-2,2-difluoro-1-methyl-O-benzoyl-4-pentyl(benzyloxycarbonyl)amine

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