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

Base Information

• Chemical Name: (2R,3R,4R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopentan-1-one
• CAS No.: 1373313-83-7
• Molecular Formula: C₂₆H₃₄O₄Si
• Molecular Weight: 438.639
• Mol file: 1373313-83-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2R,3R,4R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopentan-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: 99.0%

(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one (1373313-80-4) → (2R,3R,4R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopentan-1-one (1373313-83-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 48h; diastereospecific reaction;

DOI:10.1021/ol300667q

Reference yield:

(-)-(1R)-1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol (141436-58-0,126113-84-6) → (2R,3R,4R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopentan-1-one (1373313-83-7)

Guidance literature:

Multi-step reaction with 8 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

8.1: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 20 °C

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; tetrapropylammonium perruthennate; sodium perborate tetrahydrate; palladium 10% on activated carbon; hydrogen; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol300667q

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (2R,3R,4R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopentan-1-one (1373313-83-7)

Guidance literature:

Multi-step reaction with 10 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: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

5.1: Grubbs catalyst first generation / dichloromethane / 24 h

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

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

8.1: 1H-imidazole / dichloromethane / 0.5 h / -10 - 0 °C

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

10.1: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 20 °C

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; tetrapropylammonium perruthennate; sodium perborate tetrahydrate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol300667q

upstream raw materials:

(3aS,4S,6aR)-4,6a-dihydro-6-(2-hydroxyethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4-ol

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

(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

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

Downstream raw materials:

C₂₆H₃₃FO₄Si