(E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile

Base Information

Chemical Name:(E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile
CAS No.:866148-38-1
Molecular Formula:C₂₇H₄₁NOSi
Molecular Weight:423.714
Hs Code.:

Synonyms:(E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile

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Chemical Property of (E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile

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Technology Process of (E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile

There total 10 articles about (E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile 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: 77.0%

: 866148-49-4
(E)-(3R,8R)-8-Hydroxy-3,8-dimethyl-5,7-dimethylene-11-phenyl-undec-10-enenitrile

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 866148-38-1
(E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile

Guidance literature:: With triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ol051544e

Reference yield:

: 866148-44-9
(R)-2-Methyl-4-trimethylsilanylmethyl-pent-4-en-1-ol

: 866148-38-1
(E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 65 percent / TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

3.1: SOCl₂; pyridine / toluene / 0.5 h / -78 °C

3.2: TBAF / tetrahydrofuran / 0 - 20 °C

4.1: 81 percent / PPh₃; DEAD / diethyl ether; toluene / 0 - 20 °C

5.1: 77 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

With pyridine; thionyl chloride; titanium tetrachloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In diethyl ether; dichloromethane; toluene; 4.1: Mitsunobu reaction;
DOI:10.1021/ol051544e

Reference yield:

: 866148-45-0
(E)-(R)-3-Hydroxy-3-methyl-6-phenyl-hex-5-en-2-one

: 866148-38-1
(E)-(3R,8R)-3,8-Dimethyl-5,7-dimethylene-11-phenyl-8-triethylsilanyloxy-undec-10-enenitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: 81 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 65 percent / TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

3.1: SOCl₂; pyridine / toluene / 0.5 h / -78 °C

3.2: TBAF / tetrahydrofuran / 0 - 20 °C

4.1: 81 percent / PPh₃; DEAD / diethyl ether; toluene / 0 - 20 °C

5.1: 77 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

With pyridine; thionyl chloride; titanium tetrachloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In diethyl ether; dichloromethane; toluene; 4.1: Mitsunobu reaction;
DOI:10.1021/ol051544e