(2Z)-(5R)-[2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Base Information

• Chemical Name: (2Z)-(5R)-[2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
• CAS No.: 272776-95-1
• Molecular Formula: C₂₇H₃₇O₂PSi
• Molecular Weight: 452.649
• Mol file: 272776-95-1.mol

Synonyms:(2Z)-(5R)-[2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2Z)-(5R)-[2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide 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:

{2-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane → (2Z)-(5R)-[2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (272776-95-1)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; hexane; chloroform; at 20 ℃; for 0.5h;

DOI:10.1016/S0039-128X(00)00087-8

Reference yield:

1-(4-methoxybenzyloxy)-4-[(2S)-oxiran-2-yl]-2-butyne (272776-88-2) → (2Z)-(5R)-[2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (272776-95-1)

Guidance literature:

Multi-step reaction with 9 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

7.1: 44 mg / dimethyl sulfide; N-chlorosuccinimide / CH₂Cl₂ / 1 h / 20 °C

8.1: BuLi / hexane; tetrahydrofuran / 0.17 h / 0 °C

8.2: hexane; tetrahydrofuran / 1 h / -50 °C

9.1: aq. H₂O₂ / hexane; tetrahydrofuran; CHCl₃ / 0.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; dimethylsulfide; dihydrogen peroxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; 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 / 7.1: Chlorination / 8.1: deprotonation / 8.2: Condensation / 9.1: Oxidation;

DOI:10.1016/S0039-128X(00)00087-8

Reference yield:

5-(tert-butyl-dimethyl-silanyloxy)-non-8-en-2-ynal → (2Z)-(5R)-[2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (272776-95-1)

Guidance literature:

Multi-step reaction with 6 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

4.1: 44 mg / dimethyl sulfide; N-chlorosuccinimide / CH₂Cl₂ / 1 h / 20 °C

5.1: BuLi / hexane; tetrahydrofuran / 0.17 h / 0 °C

5.2: hexane; tetrahydrofuran / 1 h / -50 °C

6.1: aq. H₂O₂ / hexane; tetrahydrofuran; CHCl₃ / 0.5 h / 20 °C

With sodium tetrahydroborate; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; dimethylsulfide; dihydrogen peroxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene; acetonitrile; 1.1: Reduction / 2.1: hydroalumination / 2.2: Iodination / 3.1: Cyclization / 4.1: Chlorination / 5.1: deprotonation / 5.2: Condensation / 6.1: Oxidation;

DOI:10.1016/S0039-128X(00)00087-8

upstream raw materials:

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

(5R)-5-(t-butyldimethylsilyl)oxynona-8-en-2-yn-1-ol

(2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane

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

Downstream raw materials:

(5Z,7E)-(3R,24R)-3,24,25-tri(t-butyldimethylsilyl)oxy-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene

(5Z,7E)-(3R,24R)-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene-3,24,25-triol