(E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-1-ol

Base Information

Chemical Name:(E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-1-ol
CAS No.:883877-31-4
Molecular Formula:C₃₅H₆₆O₅Si₂
Molecular Weight:623.077
Hs Code.:

Synonyms:(E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-1-ol

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Chemical Property of (E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-1-ol

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Technology Process of (E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-1-ol

There total 10 articles about (E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-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: 99.0%

: 883877-72-3
(E)-(2R,3R,4R,7S,8S)-1,3-O-(4-methoxybenzylidene)-7-(triisopropylsilanyloxy)-8-(tert-butyldimethylsilanyloxy)-2,4,6-trimethylnon-5-ene

: 883877-31-4
(E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; toluene; at -78 - 0 ℃;
DOI:10.1021/ol0600786

Reference yield: 79.0%

: 883877-41-6
(E)-(2R,3R,4R,7S,8S)-1,8-di(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-ene

: 883877-31-4
(E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-1-ol

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/ol0600786

Reference yield:

: (2R,4R)-1-(tert-butyldimethylsilanyloxy)-2,4-dimethyl-5-heptyn-3-ol

: 883877-31-4
(E)-(2R,3R,4R,7S,8S)-8-(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-7-(tri-isopropylsilanyloxy)-2,4,6-trimethylnon-5-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 48 h / 20 °C

1.2: 103 mg / TBAF / tetrahydrofuran / 20 °C

2.1: n-BuLi; c-C₅H₉MgCl / Ti(OiPr)3Cl / toluene; hexane; diethyl ether / 1 h / -40 °C

2.2: BF₃*OEt₂ / toluene; hexane; diethyl ether / 1 h / -78 °C

2.3: 232 mg / DDQ / CH₂Cl₂ / 0.33 h / 0 °C

3.1: 92 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4.1: 92 percent / DIBAL / hexane; CH₂Cl₂ / 0.17 h / -78 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6.1: 99 percent / DIBAL / toluene; hexane / -78 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; sodium hydride; diisobutylaluminium hydride; cyclopentylmagnesium chloride; Dess-Martin periodane; triisopropoxytitanium(IV) chloride; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Dess-Martin oxidation;
DOI:10.1021/ol0600786