(E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone

Base Information

• Chemical Name: (E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone
• CAS No.: 1360618-75-2
• Molecular Formula: C₂₂H₂₃ClO₃
• Molecular Weight: 370.876

Synonyms:(E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone

Chemical Property of (E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone

Chemical Property:

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Technology Process of (E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone

There total 3 articles about (E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone 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: 75.0%

(E)-1-C-phenyl-2,3-dideoxy-4,5-O-isopropylidene-D-glycero-pent-2-enose (222626-15-5) + 2-(4-chlorophenyl)vinyl boronic acid → (E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone (1360618-75-2)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; at 20 ℃; for 18h; optical yield given as %de; diastereoselective reaction;

DOI:10.1021/ol300272j

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone (1360618-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 3 h / Reflux

2: trifluoroacetic anhydride / dichloromethane / 18 h / 20 °C

With trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol300272j

Reference yield:

1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3) → (E)-(3R,4R,5S)-{4-[2-(4-chlorophenyl)vinyl]-5-hydroxy-2,2-dimethyltetrahydropyran-3-yl}phenylmethanone (1360618-75-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium periodate; sodium hydrogencarbonate / water / 2 h / 35 °C

2: tetrahydrofuran / 3 h / Reflux

3: trifluoroacetic anhydride / dichloromethane / 18 h / 20 °C

With sodium periodate; sodium hydrogencarbonate; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol300272j

upstream raw materials:

2,3-isopropylidene-glyceraldehyde

(E)-1-C-phenyl-2,3-dideoxy-4,5-O-isopropylidene-D-glycero-pent-2-enose

1,2:5,6-di-O-isopropylidene-D-mannitol

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