(-)-(2S,3S,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-pentyl-4-(p-tolylsulfonyl)tetrahydrofuran

Base Information

Chemical Name:(-)-(2S,3S,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-pentyl-4-(p-tolylsulfonyl)tetrahydrofuran
CAS No.:951133-90-7
Molecular Formula:C₂₃H₃₈O₅SSi
Molecular Weight:454.703
Hs Code.:

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

Suppliers and Price of (-)-(2S,3S,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-pentyl-4-(p-tolylsulfonyl)tetrahydrofuran

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

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

There total 11 articles about (-)-(2S,3S,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-pentyl-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: 97.0%

: 951133-89-4
(-)-(2R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-pentyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran

: 951133-90-7
(-)-(2S,3S,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-pentyl-4-(p-tolylsulfonyl)tetrahydrofuran

Guidance literature:: With KOOt-Bu; In tetrahydrofuran; at -40 - 0 ℃;
DOI:10.1016/j.tetlet.2007.07.058

Reference yield:

: 951133-45-2
(+)-(5S,S(S))-(4E)-4-(p-tolylsulfinyl)deca-1,3-dien-5-ol

: 951133-90-7
(-)-(2S,3S,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-pentyl-4-(p-tolylsulfonyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / Et₃N; DMAP / dimethylformamide / 0 - 20 °C

2: 60 percent / NH₄OAc; H₂O₂ / (R,R)-JC catalyst / CH₂Cl₂; methanol / 48 h / 0 °C

3: imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

4: 97 percent / KOOt-Bu / tetrahydrofuran / -40 - 0 °C

With 1H-imidazole; dmap; ammonium acetate; dihydrogen peroxide; triethylamine; (R,R)-JC catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2: Jacobsen epoxidation;
DOI:10.1016/j.tetlet.2007.07.058

Reference yield:

: 66-25-1
hexanal

: 951133-90-7
(-)-(2S,3S,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-pentyl-4-(p-tolylsulfonyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1: LDA

2: 89 percent / Et₃N; DMAP / dimethylformamide / 0 - 20 °C

3: 60 percent / NH₄OAc; H₂O₂ / (R,R)-JC catalyst / CH₂Cl₂; methanol / 48 h / 0 °C

4: imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

5: 97 percent / KOOt-Bu / tetrahydrofuran / -40 - 0 °C

With 1H-imidazole; dmap; ammonium acetate; dihydrogen peroxide; triethylamine; lithium diisopropyl amide; (R,R)-JC catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3: Jacobsen epoxidation;
DOI:10.1016/j.tetlet.2007.07.058