(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester

Base Information

Chemical Name:(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester
CAS No.:343262-86-2
Molecular Formula:C₃₆H₄₆O₅Si
Molecular Weight:586.844
Hs Code.:

Synonyms:(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester

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Chemical Property of (2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester

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Technology Process of (2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester

There total 10 articles about (2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-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: 88.0%

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

: 343262-85-1
(E)-(4S,5R,6S)-5-(tert-butyldiphenylsilanoxy)-3-(4-methoxybenzyloxy)-4-methyloct-6-enal

: 343262-86-2
(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester

Guidance literature:: In dichloromethane; for 1.5h;
DOI:10.1021/ol015753k

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 343262-86-2
(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / CSA / CH₂Cl₂ / 40 h

2: 74 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 20 h

3: 100 percent / NaIO₄ / H₂O; tetrahydrofuran / 0.5 h

4: 88 percent / CH₂Cl₂ / 1.5 h

With sodium periodate; AD-mix-α; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 4: Wittig olefination;
DOI:10.1021/ol015753k

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 343262-86-2
(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 99 percent / imidazole / CH₂Cl₂ / 20 h

2: 86 percent / LiBH₄ / diethyl ether; H₂O / -20 - 5 °C

3: 98 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - -30 °C

4: 85 percent / diethyl ether / 3 h / -78 °C

5: 67 percent / CSA / CH₂Cl₂ / 40 h

6: 74 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 20 h

7: 100 percent / NaIO₄ / H₂O; tetrahydrofuran / 0.5 h

8: 88 percent / CH₂Cl₂ / 1.5 h

With 1H-imidazole; sodium periodate; AD-mix-α; lithium borohydride; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol; 3: Swern oxidation / 8: Wittig olefination;
DOI:10.1021/ol015753k