(3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol

Base Information

• Chemical Name: (3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol
• CAS No.: 1375478-74-2
• Molecular Formula: C₃₇H₆₂O₄Si₂
• Molecular Weight: 627.068

Synonyms:(3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol

Chemical Property of (3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol

There total 10 articles about (3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol 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: 53.0%

(3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-isopropyl-5-oxopentyl benzoate (1375478-69-5) + (E)-tert-butyl((6-iodohept-5-en-1-yl)oxy)diphenylsilane (1375478-71-9) → (3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol (1375478-74-2) + (3R,4R,5R,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol (1375478-75-3)

Guidance literature:

(E)-tert-butyl((6-iodohept-5-en-1-yl)oxy)diphenylsilane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.0833333h; Inert atmosphere;

(3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-isopropyl-5-oxopentyl benzoate; In diethyl ether; pentane; at 0 ℃; for 0.666667h; Inert atmosphere;

With ethylmagnesium bromide; In diethyl ether; pentane; at 0 - 20 ℃; for 3.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/anie.201108564

Reference yield:

(3R,4R)-4-((tert-butyldimethylsilyl)oxy)-5-hydroxy-3-isopropylpentyl benzoate (1375478-68-4) → (3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol (1375478-74-2)

Guidance literature:

Multi-step reaction with 2 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

With oxalyl dichloride; tert.-butyl lithium; dimethyl sulfoxide; In diethyl ether; dichloromethane; pentane;

DOI:10.1002/anie.201108564

Reference yield:

C18H26O4 (1375478-65-1) → (3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol (1375478-74-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water; acetic acid / 2 h / 20 - 50 °C

2.1: 1H-imidazole; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: pyridine; hydrogen fluoride / tetrahydrofuran / 7 h / 0 - 20 °C / Inert atmosphere

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

4.2: -78 - 20 °C / Inert atmosphere

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

5.2: 0.67 h / 0 °C / Inert atmosphere

5.3: 3.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; oxalyl dichloride; hydrogen fluoride; water; tert.-butyl lithium; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; 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

Downstream raw materials:

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

methyl (1R,2S,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-2-(4-((tert-butyldiphenylsilyl)oxy)butyl)-6-isopropyl-3-methylcyclohex-3-enecarboxylate

C₃₇H₅₈O₄Si₂

methyl (1R,2S,5R,6S)-5-hydroxy-2-(4-hydroxybutyl)-6-isopropyl-3-methylcyclohex-3-enecarboxylate

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