(1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate

Base Information

Chemical Name:(1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate
CAS No.:935684-22-3
Molecular Formula:C₁₉H₂₂F₅IO₃Si
Molecular Weight:548.364
Hs Code.:

Synonyms:(1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate

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Chemical Property of (1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate

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Technology Process of (1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate

There total 7 articles about (1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate 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: 91.0%

: 935684-21-2
(1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-en-1-ol

pentafluorobenzoylchloride: 2251-50-5
pentafluorobenzoylchloride

: 935684-22-3
(1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate

Guidance literature:: With pyridine; dmap; In diethyl ether; at 25 ℃; for 2h;
DOI:10.1021/ol063052n

Reference yield:

: 10288-24-1
3-methyl-4-hydroxy-2-cyclopentenone

: 935684-22-3
(1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: porcine pancreatic lipase; vinyl acetate / 25 °C

1.2: guanidine / methanol / 0.08 h

2.1: imidazole / dimethylformamide / 12 h / 25 °C

3.1: I₂; PDC / CH₂Cl₂ / 48 h / 25 °C

4.1: BH₃*PhNEt₂ / diphenyl((S)-pyrrolidin-2-yl)methanol; B(OMe)3 / tetrahydrofuran / 1.5 h / 25 °C

5.1: 91 percent / DMAP; pyridine / diethyl ether / 2 h / 25 °C

With pyridine; 1H-imidazole; dmap; dipyridinium dichromate; borane N,N-diethylaniline complex; vinyl acetate; porcine pancreatic lipase; iodine; Trimethyl borate; (S)-diphenylprolinol; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol063052n

Reference yield:

: 935684-23-4
4-[tert-butyl(dimethyl)silyl]oxy-3-methylcyclopent-2-en-1-one

: 935684-22-3
(1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-enyl 2,3,4,5,6-pentafluorobenzoate

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / I₂; PDC / CH₂Cl₂ / 46 h / 25 °C

2: 49 percent / BH₃*PhNEt₂ / diphenyl((S)-pyrrolidin-2-yl)methanol; B(OMe)3 / tetrahydrofuran / 1.5 h / 25 °C

3: 91 percent / DMAP; pyridine / diethyl ether / 2 h / 25 °C

With pyridine; dmap; dipyridinium dichromate; borane N,N-diethylaniline complex; iodine; Trimethyl borate; (S)-diphenylprolinol; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol063052n