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

Base Information

Chemical Name:(-)-(2R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-pentyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran
CAS No.:951133-89-4
Molecular Formula:C₂₃H₃₈O₄SSi
Molecular Weight:438.704
Hs Code.:

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

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Chemical Property of (-)-(2R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-pentyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran

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Technology Process of (-)-(2R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-pentyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran

There total 9 articles about (-)-(2R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-pentyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran 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: 17.0%

: (5S)-5-pentyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran-2-methanol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1092556-09-6
(-)-(2S,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-pentyl-4-(p-tolylsulfonyl)-2,5-dihydrofuran

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

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 14h; Inert atmosphere;
DOI:10.1021/jo801803m

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 66-25-1
hexanal

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

Guidance literature:: Multi-step reaction with 4 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

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