(2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene

Base Information

Chemical Name:(2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene
CAS No.:1373313-89-3
Molecular Formula:C₂₆H₃₂O₃Si
Molecular Weight:420.624
Hs Code.:

Synonyms:(2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene

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Chemical Property of (2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene

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Technology Process of (2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene

There total 7 articles about (2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene 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: 90.0%

: 1373313-77-9
(3aS,4S,6aR)-2,2-dimethyl-6-vinyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1373313-89-3
(2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene

Guidance literature:: With 1H-imidazole; In dichloromethane; at -10 - 20 ℃; for 10h;
DOI:10.1021/ol300667q

Reference yield:

: (3aS,6S,6aS)-2,2-dimethyl-6-vinyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

: 1373313-89-3
(2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium; lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 12.5 h / -78 - 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: Grubbs catalyst first generation / dichloromethane / 24 h

3.1: 1H-imidazole / dichloromethane / 10 h / -10 - 20 °C

With 1H-imidazole; Grubbs catalyst first generation; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol300667q

Reference yield:

: 141436-58-0,126113-84-6
(-)-(1R)-1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol

: 1373313-89-3
(2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium periodate / dichloromethane / 1 h / 0 - 20 °C

2.1: n-butyllithium; lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 12.5 h / -78 - 20 °C / Inert atmosphere

2.3: Inert atmosphere

3.1: Grubbs catalyst first generation / dichloromethane / 24 h

4.1: 1H-imidazole / dichloromethane / 10 h / -10 - 20 °C

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol300667q