(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

Base Information

Chemical Name:(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one
CAS No.:1373313-80-4
Molecular Formula:C₂₆H₃₂O₄Si
Molecular Weight:436.623
Hs Code.:

Synonyms:(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

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Chemical Property of (2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

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Technology Process of (2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

There total 10 articles about (2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one 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: 92.0%

: 1373313-78-0
(1S,4R,5S)-3-[2-(tert-butyldiphenylsilyloxy)ethyl]-4,5-(O-isopropylidenedioxy)cyclopent-2⁽³⁾en-1-ol(1S,4R,5S)-3-[2-(tert-butyldiphenylsilyloxy)ethyl]-4,5-(O-isopropylidenedioxy)cyclopent-2⁽³⁾en-1-ol

: 1373313-80-4
(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

Guidance literature:: With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere; Molecular sieve;
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

: 1373313-80-4
(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

Guidance literature:: Multi-step reaction with 7 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: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

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

6.1: 1H-imidazole / dichloromethane / 0.5 h / -10 - 0 °C

7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; tetrapropylammonium perruthennate; sodium perborate tetrahydrate; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol300667q

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 1373313-80-4
(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: tetrahydrofuran / 6 h / -78 - 20 °C

1.2: 0 °C

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

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

3.2: 12.5 h / -78 - 20 °C / Inert atmosphere

3.3: Inert atmosphere

4.1: Grubbs catalyst first generation / dichloromethane / 24 h

5.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

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

7.1: 1H-imidazole / dichloromethane / 0.5 h / -10 - 0 °C

8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; tetrapropylammonium perruthennate; sodium perborate tetrahydrate; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol300667q