(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-one

Base Information

• Chemical Name: (4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-one
• CAS No.: 1375478-77-5
• Molecular Formula: C₃₇H₅₈O₄Si₂
• Molecular Weight: 623.036

Synonyms:(4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-one

Chemical Property of (4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-one

There total 11 articles about (4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-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: 85.0%

(3R,4R,5R,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol (1375478-75-3) → (4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-one (1375478-77-5)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201108564

Reference yield:

(3R,4R)-4-((tert-butyldimethylsilyl)oxy)-5-hydroxy-3-isopropylpentyl benzoate (1375478-68-4) → (4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-one (1375478-77-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere

2.2: 0.67 h / 0 °C / Inert atmosphere

2.3: 3.5 h / 0 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere

With oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tert.-butyl lithium; dimethyl sulfoxide; In diethyl ether; dichloromethane; pentane;

DOI:10.1002/anie.201108564

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (4R,5R,6R)-5-((tert-butyldimethylsilyl)oxy)-6-((E)-7-((tert-butyldiphenylsilyl)oxy)hept-2-en-2-yl)-4-isopropyltetrahydro-2H-pyran-2-one (1375478-77-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

2.2: 3.5 h / -78 - 20 °C / Inert atmosphere

3.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran; n-heptane / 1 h / 0 - 65 °C / Inert atmosphere; Darkness

3.2: 0.25 h / -78 °C / Inert atmosphere

4.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere

4.2: 0.67 h / 0 °C / Inert atmosphere

4.3: 3.5 h / 0 - 20 °C / Inert atmosphere

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; zirconocene dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tert.-butyl lithium; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; n-heptane; dichloromethane; pentane;

DOI:10.1002/anie.201108564

upstream raw materials:

C₁₈H₂₆O₄

C₁₅H₂₂O₄

(3R,4R)-4-((tert-butyldimethylsilyl)oxy)-5-hydroxy-3-isopropylpentyl benzoate

ethyl (R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylpentanoate

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