(-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran

Base Information

• Chemical Name: (-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran
• CAS No.: 873438-24-5
• Molecular Formula: C₂₄H₃₂O₅SSi
• Molecular Weight: 460.667

Synonyms:(-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran

Chemical Property of (-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran

Chemical Property:

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Technology Process of (-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran

There total 3 articles about (-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran 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: 83.0%

tert-Butyl-dimethyl-[(2S,5R)-5-phenyl-4-(toluene-4-sulfonyl)-2,5-dihydro-furan-2-ylmethoxy]-silane (873438-22-3) → (-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran (873438-24-5)

Guidance literature:

With tert.-butylhydroperoxide; di-tert-butyl peroxide; potassium hydride; In tetrahydrofuran; at 0 ℃; for 1.25h;

DOI:10.1021/jo051459k

Reference yield:

[(5R)-5-phenyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran-2-yl]methanol → (-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran (873438-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 34 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 83 percent / tert-butyl hycdroperoxide; KH; di(tert-butyl) peroxide / tetrahydrofuran / 1.25 h / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; di-tert-butyl peroxide; potassium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo051459k

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (-)-(2R,3R,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran (873438-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 34 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 83 percent / tert-butyl hycdroperoxide; KH; di(tert-butyl) peroxide / tetrahydrofuran / 1.25 h / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; di-tert-butyl peroxide; potassium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo051459k

upstream raw materials:

tert-Butyl-dimethyl-[(2S,5R)-5-phenyl-4-(toluene-4-sulfonyl)-2,5-dihydro-furan-2-ylmethoxy]-silane

tert-butyldimethylsilyl chloride

Downstream raw materials:

(+)-(2R,5S)-5-(tert-butyldimethylsilyloxymethyl)-2-phenyl-3-oxotetrahydrofuran

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