6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester

Base Information

Chemical Name:6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester
CAS No.:847835-00-1
Molecular Formula:C₂₉H₄₄O₆Si
Molecular Weight:516.75
Hs Code.:

Synonyms:6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester

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Chemical Property of 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester

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Technology Process of 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester

There total 21 articles about 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl 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: 92.0%

: 856410-59-8
(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 847835-00-1
6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester

Guidance literature:: In benzene; at 20 ℃;
DOI:10.1002/anie.200500029

Reference yield: 90.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 847835-09-0
6-hydroxy-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester

: 847835-00-1
6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.12.056

Reference yield:

: (2E,5Z)-(S)-1-{(4S,5S)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hepta-2,5-diene-1,7-diol

: 847835-00-1
6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / PdCl₂(CH₃CN)2 / tetrahydrofuran / 3 h / 0 °C

2: 89 percent / HCl / methanol / 20 °C

3: 87 percent / DDQ / CH₂Cl₂ / 0 °C

4: 90 percent / imidazole / dimethylformamide / 20 °C

5: 83 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 96 percent / Dess-Martin periodinane

7: 92 percent / benzene / 20 °C

With 1H-imidazole; hydrogenchloride; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 6: Dess-Martin oxidation / 7: Wittig reaction;
DOI:10.1002/anie.200500029