(2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene

Base Information

Chemical Name:(2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene
CAS No.:889454-45-9
Molecular Formula:C₃₇H₆₅BrO₆Si₂
Molecular Weight:741.995
Hs Code.:

(2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene

Synonyms:(2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene

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Chemical Property of (2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene

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Technology Process of (2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene

There total 6 articles about (2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene 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: 96.0%

: 889454-55-1
(2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-trien-5-ol

: trimethyloxonium tetrafluoroborate

: 889454-45-9
(2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene

Guidance literature:: With Proton Sponge; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol060609q

Reference yield:

: 889454-41-5
(R)-3-(3,4-dimethoxybenzyloxy)-2-methylbutan-3-one

: 889454-45-9
(2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / samarium diiodide / tetrahydrofuran / 1 h / -10 °C

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

3: 87 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

4: 96 percent / Proton Sponge / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; samarium diiodide; Proton Sponge; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol060609q

Reference yield:

: 889454-42-6
(2R,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-hydroxy-13-bromo-2,7-dimethyl-trideca-6,10,12-trien-3-one

: 889454-45-9
(2R,3S,5S,6E,9R,10E,12E)-9-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxybenzyloxy)-5-methoxy-13-bromo-2,7-dimethyl-3-triethylsilyloxy-trideca-6,10,12-triene

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / samarium diiodide / tetrahydrofuran / 1 h / -10 °C

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

3: 87 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

4: 96 percent / Proton Sponge / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; samarium diiodide; Proton Sponge; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol060609q