anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol

Base Information

Chemical Name:anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol
CAS No.:916461-47-7
Molecular Formula:C₃₃H₄₈O₂Si
Molecular Weight:504.828
Hs Code.:

Synonyms:anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol

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Chemical Property of anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol

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Technology Process of anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol

There total 6 articles about anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol 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: 73.0%

: 916461-46-6
anti-((3R,4R,5E,7E)-2-(bromomethyl)-3,5,7,9,9-pentamethyl-1,5,7-trien-4-yloxy)(tert-butyl)diphenylsilane

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 916461-47-7
anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol

Guidance literature:: With indium; lanthanum(lll) triflate; In tetrahydrofuran; water; at 20 ℃; for 96h;
DOI:10.1039/b608193m

Reference yield:

: 916461-56-8
anti-(3R,4R,5E,7E)-3,5,7,9,9-pentamethyl-2-methylenedeca-5,7-diene-1,4-diol

: 916461-47-7
anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / triethyl amine; 4-dimethylamino pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 78 percent / AgNO₃ / dimethylformamide / 12 h / 0 - 20 °C

3: 94 percent / K₂CO₃ / methanol / 16 h / 20 °C

4: 74 percent / NBS; triphenylphosphine / CH₂Cl₂ / 0.75 h / -78 - 0 °C

5: 73 percent / indium; La(OTf)3 / H₂O; tetrahydrofuran / 96 h / 20 °C

With dmap; indium; N-Bromosuccinimide; potassium carbonate; silver nitrate; triethylamine; triphenylphosphine; lanthanum(lll) triflate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1039/b608193m

Reference yield:

: anti-ethyl (3R,4R,5E,7E)-4-hydroxy-3,5,7,9,9-pentamethyl-2-methylenedeca-5,7-dienyl carbonate

: 916461-47-7
anti-(4R,5R,6E,8E)-5-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / AgNO₃ / dimethylformamide / 12 h / 0 - 20 °C

2: 94 percent / K₂CO₃ / methanol / 16 h / 20 °C

3: 74 percent / NBS; triphenylphosphine / CH₂Cl₂ / 0.75 h / -78 - 0 °C

4: 73 percent / indium; La(OTf)3 / H₂O; tetrahydrofuran / 96 h / 20 °C

With indium; N-Bromosuccinimide; potassium carbonate; silver nitrate; triphenylphosphine; lanthanum(lll) triflate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1039/b608193m