[3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol

Base Information

Chemical Name:[3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol
CAS No.:1373313-90-6
Molecular Formula:C₂₆H₃₄O₄Si
Molecular Weight:438.639
Hs Code.:

Synonyms:[3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol

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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 [3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol

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Technology Process of [3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol

There total 11 articles about [3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol 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: 78.0%

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

: 1373313-90-6
[3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol

Guidance literature:: (2R,3R,4S)-4-(tert-butyldiphenylsilyloxy)-1-ethenyl-2,3-(O-isopropylidenedioxy)-1-cyclopentene; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

With water; In tetrahydrofuran; at 20 ℃; for 15h;

Reference yield:

: C₃₄H₄₇BO₃Si

: 1373313-90-6
[3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol

Guidance literature:: With sodium perborate tetrahydrate; In tetrahydrofuran; water; at 20 ℃; for 15h; Inert atmosphere;
DOI:10.1021/ol300667q

Reference yield:

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

: 1373313-90-6
[3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol

Guidance literature:: Multi-step reaction with 4 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: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

4.1: sodium perborate tetrahydrate / tetrahydrofuran; water / 15 h / 20 °C / Inert atmosphere

With Grubbs catalyst first generation; n-butyllithium; sodium perborate tetrahydrate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol300667q