(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

Base Information

• Chemical Name: (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
• CAS No.: 1373313-78-0
• Molecular Formula: C₂₆H₃₄O₄Si
• Molecular Weight: 438.639
• Mol file: 1373313-78-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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: 60.0%

(3aS,4S,6aR)-4,6a-dihydro-6-(2-hydroxyethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4-ol (858360-41-5) + tert-butylchlorodiphenylsilane (58479-61-1) → (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 (1373313-78-0) + (2R,3R,4S)-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-(tert-butyldiphenylsilyloxy)-2,3-(O-isopropylidenedioxy)-1-cyclopentene (1373313-79-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at -10 - 0 ℃; for 0.5h;

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) → (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 (1373313-78-0) + (2R,3R,4S)-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-(tert-butyldiphenylsilyloxy)-2,3-(O-isopropylidenedioxy)-1-cyclopentene (1373313-79-1)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; sodium perborate tetrahydrate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

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) → (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 (1373313-78-0) + (2R,3R,4S)-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-(tert-butyldiphenylsilyloxy)-2,3-(O-isopropylidenedioxy)-1-cyclopentene (1373313-79-1)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; sodium perborate tetrahydrate; lithium diisopropyl amide; In tetrahydrofuran; 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

tert-butylchlorodiphenylsilane

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

2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

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

(2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one

(2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

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