(2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

Base Information

Chemical Name:(2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester
CAS No.:878132-05-9
Molecular Formula:C₃₈H₅₈O₅Si₂
Molecular Weight:651.047
Hs Code.:

(2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

Synonyms:(2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

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Chemical Property of (2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

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Technology Process of (2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

There total 10 articles about (2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester 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: 94.0%

: 878132-04-8
(Z)-3-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-propenal

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 878132-05-9
(2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

Guidance literature:: In toluene; at 130 ℃; for 43h;
DOI:10.1021/ol0527678

Reference yield:

: (3S,4R,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-3-methyl-tetrahydro-pyran-2-one

: 878132-05-9
(2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 91 percent / 2,6-lutidine / dimethylformamide / 3.5 h / 20 °C

2: 90 percent / nBuLi / tetrahydrofuran; hexane / 3 h / -78 °C

3: 90 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -30 °C

4: 100 percent / H₂ / Pd/C / ethanol / 48 h

5: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

6: 88 percent / NaI; DBU / tetrahydrofuran / 1.75 h / -78 - 0 °C

7: 98 percent / DIBALH / CH₂Cl₂; hexane / 0.17 h / -78 °C

8: 99 percent / MnO₂ / CH₂Cl₂; benzene / 24 h / 20 °C

9: 94 percent / toluene / 43 h / 130 °C

With 2,6-dimethylpyridine; triethylsilane; manganese(IV) oxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 5: Dess-Martin oxidation;
DOI:10.1021/ol0527678

Reference yield:

: 878132-00-4
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

: 878132-05-9
(2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / nBuLi / tetrahydrofuran; hexane / 3 h / -78 °C

2: 90 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -30 °C

3: 100 percent / H₂ / Pd/C / ethanol / 48 h

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5: 88 percent / NaI; DBU / tetrahydrofuran / 1.75 h / -78 - 0 °C

6: 98 percent / DIBALH / CH₂Cl₂; hexane / 0.17 h / -78 °C

7: 99 percent / MnO₂ / CH₂Cl₂; benzene / 24 h / 20 °C

8: 94 percent / toluene / 43 h / 130 °C

With triethylsilane; manganese(IV) oxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; benzene; 4: Dess-Martin oxidation;
DOI:10.1021/ol0527678