1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4⁽⁵⁾en]-(6-chloropurine-9-yl)

Base Information

• Chemical Name: 1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4⁽⁵⁾en]-(6-chloropurine-9-yl)
• CAS No.: 1373313-86-0
• Molecular Formula: C₃₁H₃₅ClN₄O₃Si
• Molecular Weight: 575.182
• Mol file: 1373313-86-0.mol

Synonyms:1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4⁽⁵⁾en]-(6-chloropurine-9-yl)

Chemical Property of 1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4⁽⁵⁾en]-(6-chloropurine-9-yl)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4⁽⁵⁾en]-(6-chloropurine-9-yl)

There total 11 articles about 1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4⁽⁵⁾en]-(6-chloropurine-9-yl) 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: 9.0%

(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 (1373313-78-0) + 6-chloro-7H-purine (87-42-3,111055-92-6) → C31H35ClN4O3Si (1373313-87-1) + 1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4(5)en]-(6-chloropurine-9-yl) (1373313-86-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 12.25h;

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) → C31H35ClN4O3Si (1373313-87-1) + 1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4(5)en]-(6-chloropurine-9-yl) (1373313-86-0)

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: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12.25 h / 0 - 20 °C

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; di-isopropyl azodicarboxylate; sodium perborate tetrahydrate; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; 8.1: Mitsunobu 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) → C31H35ClN4O3Si (1373313-87-1) + 1-[ (1R,2S,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(ter t-butyldiphenylsilyloxy)ethyl]cyclopent-4(5)en]-(6-chloropurine-9-yl) (1373313-86-0)

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: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12.25 h / 0 - 20 °C

With 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; di-isopropyl azodicarboxylate; sodium perborate tetrahydrate; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; 7.1: Mitsunobu reaction;

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

6-chloro-7H-purine