(8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-one

Base Information

Chemical Name:(8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-one
CAS No.:157394-84-8
Molecular Formula:C₅₂H₆₆O₄Si₂
Molecular Weight:811.265
Hs Code.:

Synonyms:(8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-one

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Chemical Property of (8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-one

Chemical Property:

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Technology Process of (8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-one

There total 10 articles about (8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-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: 95.0%

: 106064-61-3
(R)-3-[(tert-butyldiphenylsilyl)oxy]pentanoic acid lactone

: 157394-82-6
tert-Butyl-[(Z)-(R)-((1E,3E)-1-hexa-1,3-dien-5-ynyl)-non-3-enyloxy]-diphenyl-silane

: 157394-84-8
(8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-one

Guidance literature:: With n-butyllithium; In tetrahydrofuran; -78 to -30 deg C, 1 h; -78 deg C, 0.5 h;
DOI:10.1016/S0040-4039(00)73170-4

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 157394-84-8
(8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-one

Guidance literature:: Multi-step reaction with 6 steps

1: AgNO₃, C₅H₅N / CH₂Cl₂ / 3 h / 23 °C

2: 1.) Tf₂O; 2.) DBU / 1.) C₅H₅N, CH₂Cl₂, 0 deg C, 2 h; 2.) 23 deg C, 10 h

3: H₂ / 10 percent Pd/C / ethyl acetate / 10 h / 23 °C / 760 Torr

4: 80 percent / HOAc, water / tetrahydrofuran / 14 h / 70 °C

5: 89 percent / PCC, Al₂O₃ / CH₂Cl₂ / 8 h / 23 °C

6: 95 percent / n-BuLi / tetrahydrofuran / -78 to -30 deg C, 1 h; -78 deg C, 0.5 h

With pyridine; aluminum oxide; n-butyllithium; trifluoromethylsulfonic anhydride; water; hydrogen; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4039(00)73170-4

Reference yield:

: 158718-95-7
2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran

: 157394-84-8
(8E,10E,14Z)-(3R,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-icosa-8,10,14-trien-6-yn-5-one

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / 10 percent Pd/C / ethyl acetate / 10 h / 23 °C / 760 Torr

2: 80 percent / HOAc, water / tetrahydrofuran / 14 h / 70 °C

3: 89 percent / PCC, Al₂O₃ / CH₂Cl₂ / 8 h / 23 °C

4: 95 percent / n-BuLi / tetrahydrofuran / -78 to -30 deg C, 1 h; -78 deg C, 0.5 h

With aluminum oxide; n-butyllithium; water; hydrogen; acetic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4039(00)73170-4