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

Base Information

• Chemical Name: tert-Butyl-dimethyl-[(2S,5R)-5-phenyl-4-(toluene-4-sulfonyl)-2,5-dihydro-furan-2-ylmethoxy]-silane
• CAS No.: 873438-22-3
• Molecular Formula: C₂₄H₃₂O₄SSi
• Molecular Weight: 444.667
• Mol file: 873438-22-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about tert-Butyl-dimethyl-[(2S,5R)-5-phenyl-4-(toluene-4-sulfonyl)-2,5-dihydro-furan-2-ylmethoxy]-silane 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: 41.0%

[(5R)-5-phenyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran-2-yl]methanol + tert-butyldimethylsilyl chloride (18162-48-6) → tert-Butyl-dimethyl-[(2R,5R)-5-phenyl-4-(toluene-4-sulfonyl)-2,5-dihydro-furan-2-ylmethoxy]-silane (873438-23-4) + tert-Butyl-dimethyl-[(2S,5R)-5-phenyl-4-(toluene-4-sulfonyl)-2,5-dihydro-furan-2-ylmethoxy]-silane (873438-22-3)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo051459k

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:

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)-3,4-epoxy-5-phenyl-4-(p-tolylsulfonyl)tetrahydrofuran-2-yl]methanol

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / tert-butyl hycdroperoxide; KH; di(tert-butyl) peroxide / tetrahydrofuran / 1.25 h / 0 °C

2: 100 percent / tetra(n-butyl)ammonium fluoride; acetic acid / tetrahydrofuran / 4.5 h / 0 - 20 °C

With tert.-butylhydroperoxide; di-tert-butyl peroxide; tetrabutyl ammonium fluoride; potassium hydride; acetic acid; In tetrahydrofuran;

DOI:10.1021/jo051459k

upstream raw materials:

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

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