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

Base Information

Chemical Name:(1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-en-1-ol
CAS No.:935684-21-2
Molecular Formula:C₁₂H₂₃IO₂Si
Molecular Weight:354.303
Hs Code.:

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

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

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Chemical Property of (1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-en-1-ol

Chemical Property:

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Technology Process of (1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-en-1-ol

There total 1 articles about (1R,4R)-4-(tert-butyldimethylsilanyloxy)-2-iodo-3-methylcyclopent-2-en-1-ol 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:

: 935684-12-1
4-{[tert-butyl(dimethyl)silyl]oxy}-2-iodo-3-methylcyclopent-2-en-1-one

pentafluorobenzoylchloride: 2251-50-5
pentafluorobenzoylchloride

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

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

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

Guidance literature:: 4-{[tert-butyl(dimethyl)silyl]oxy}-2-iodo-3-methylcyclopent-2-en-1-one; With borane N,N-diethylaniline complex; Trimethyl borate; (S)-diphenylprolinol; In tetrahydrofuran; at 25 ℃; for 1.5h;

pentafluorobenzoylchloride; With pyridine; dmap; In diethyl ether; at 25 ℃; for 2h; Title compound not separated from byproducts;
DOI:10.1021/ol063052n

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:

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

: 966-47-2
3-methoxy-estra-1,3,5⁽¹⁰⁾,8⁽⁹⁾,14⁽¹⁵⁾-pentaene-17-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / DMAP; pyridine / diethyl ether / 2 h / 25 °C

2.1: CuCN*2LiCl / tetrahydrofuran / 0.5 h / 0 °C

2.2: 66 percent / tetrahydrofuran / 25 °C

3.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.2: B(OMe)3 / tetrahydrofuran; pentane / 24 h / -78 - 25 °C

3.3: 45 percent / NaBO₃*4H₂O / tetrahydrofuran; pentane / 24 h / 25 °C

4.1: p-TsOH / benzene / 12 h / 25 °C

5.1: TBAF / tetrahydrofuran / 16 h / 25 °C

6.1: 17 mg / Celite; CrO₃ / diethyl ether; CH₂Cl₂ / 12 h / 25 °C

With pyridine; chromium(VI) oxide; dmap; n-butyllithium; Celite; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; benzene;
DOI:10.1021/ol063052n