(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol

Base Information

Chemical Name:(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol
CAS No.:343262-87-3
Molecular Formula:C₃₅H₄₆O₄Si
Molecular Weight:558.833
Hs Code.:

Synonyms:(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol

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Chemical Property of (2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol

Chemical Property:

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Technology Process of (2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol

There total 11 articles about (2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-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: 96.0%

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

: 343262-87-3
(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ol015753k

Reference yield:

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

: 343262-87-3
(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol

Guidance literature:: Multi-step reaction with 5 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

5: 96 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

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

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 343262-87-3
(2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol

Guidance literature:: Multi-step reaction with 9 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

9: 96 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

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