(1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran

Base Information

• Chemical Name: (1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran
• CAS No.: 335274-36-7
• Molecular Formula: C₃₉H₃₉O₅PSi
• Molecular Weight: 646.795

Synonyms:(1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran

Chemical Property of (1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran

Chemical Property:

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Technology Process of (1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran

There total 3 articles about (1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran 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: 81.0%

chloro-trimethyl-silane (75-77-4) + (1S,2S)-1,2-Bis(benzoyloxy)-4-diphenylphosphinoyl-1-phenylbutane (335274-29-8) → (1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran (335274-36-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 4h;

DOI:10.1039/b008500f

Reference yield:

benzoyl chloride (98-88-4) → (1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran (335274-36-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 20 °C

2: 81 percent / LDA / tetrahydrofuran; hexane / 4 h / -78 °C

With dmap; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/b008500f

Reference yield:

(1S,2S)-4-Diphenylphosphinoyl-1-phenylbutane-1,2-diol (230965-19-2) → (1'S,2R,3R,5S)-3-Diphenylphosphinoyl-5-[phenyl(benzoyloxy)methyl]-2-phenyl-2-trimethylsilyloxytetrahydrofuran (335274-36-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 20 °C

2: 81 percent / LDA / tetrahydrofuran; hexane / 4 h / -78 °C

With dmap; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/b008500f

upstream raw materials:

chloro-trimethyl-silane

(1S,2S)-1,2-Bis(benzoyloxy)-4-diphenylphosphinoyl-1-phenylbutane

benzoyl chloride

(1S,2S)-4-Diphenylphosphinoyl-1-phenylbutane-1,2-diol

Downstream raw materials:

(1'S,2'S,1''R)-{2'-[hydroxy(phenyl)methyl]cyclopropyl}(phenyl)methanone

(4S,5S)-5-benzoyloxy-1,5-diphenyl-4-diphenylphosphinyloxy-pentan-1-one

(4S,5S)-5-benzoyloxy-1,5-diphenyl-2-diphenylphosphinoyl-4-hydroxypentan-1-one

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