(2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

Base Information

Chemical Name:(2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol
CAS No.:272776-93-9
Molecular Formula:C₁₅H₂₈O₂Si
Molecular Weight:268.472
Hs Code.:

Synonyms:(2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

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Chemical Property of (2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

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Technology Process of (2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

There total 7 articles about (2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol 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: 67.0%

: 272776-92-8
(2Z)-(5R)-5-(t-butyldimethylsilyl)oxy-3-iodonona-2,8-dien-1-ol

: 272776-93-9
(2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In acetonitrile; for 4h; Heating;
DOI:10.1016/S0039-128X(00)00087-8

Reference yield:

: 272776-88-2
1-(4-methoxybenzyloxy)-4-[(2S)-oxiran-2-yl]-2-butyne

: 272776-93-9
(2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 0.67 h / -78 - 20 °C

2.1: imidazole / dimethylformamide / 3 h / 20 °C

3.1: aq. DDQ / CH₂Cl₂ / 3 h / 20 °C

4.1: NaBH₄ / methanol / 0.17 h / 0 °C

5.1: [(MeOCH₂CH₂O)2AlH₂]Na / toluene; diethyl ether / 6 h / 20 °C

5.2: 65 percent / I₂ / diethyl ether; toluene; ethyl acetate / 1.67 h / -50 - 20 °C

6.1: 67 percent / Pd(PPh₃)4; Et₃N / acetonitrile / 4 h / Heating

With 1H-imidazole; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Ring cleavage / 2.1: silylation / 3.1: oxidative cleavage / 4.1: Reduction / 5.1: hydroalumination / 5.2: Iodination / 6.1: Cyclization;
DOI:10.1016/S0039-128X(00)00087-8

Reference yield:

: 5-(tert-butyl-dimethyl-silanyloxy)-non-8-en-2-ynal

: 272776-93-9
(2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaBH₄ / methanol / 0.17 h / 0 °C

2.1: [(MeOCH₂CH₂O)2AlH₂]Na / toluene; diethyl ether / 6 h / 20 °C

2.2: 65 percent / I₂ / diethyl ether; toluene; ethyl acetate / 1.67 h / -50 - 20 °C

3.1: 67 percent / Pd(PPh₃)4; Et₃N / acetonitrile / 4 h / Heating

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In methanol; diethyl ether; toluene; acetonitrile; 1.1: Reduction / 2.1: hydroalumination / 2.2: Iodination / 3.1: Cyclization;
DOI:10.1016/S0039-128X(00)00087-8