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

Base Information

Chemical Name:(E)-(2R,3R,4R,7S,8S)-1,3-O-(4-methoxybenzylidene)-7-(triisopropylsilanyloxy)-8-(tert-butyldimethylsilanyloxy)-2,4,6-trimethylnon-5-ene
CAS No.:883877-72-3
Molecular Formula:C₃₅H₆₄O₅Si₂
Molecular Weight:621.061
Hs Code.:

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

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Chemical Property of (E)-(2R,3R,4R,7S,8S)-1,3-O-(4-methoxybenzylidene)-7-(triisopropylsilanyloxy)-8-(tert-butyldimethylsilanyloxy)-2,4,6-trimethylnon-5-ene

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Technology Process of (E)-(2R,3R,4R,7S,8S)-1,3-O-(4-methoxybenzylidene)-7-(triisopropylsilanyloxy)-8-(tert-butyldimethylsilanyloxy)-2,4,6-trimethylnon-5-ene

There total 6 articles about (E)-(2R,3R,4R,7S,8S)-1,3-O-(4-methoxybenzylidene)-7-(triisopropylsilanyloxy)-8-(tert-butyldimethylsilanyloxy)-2,4,6-trimethylnon-5-ene 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: 95.0%

: 883877-71-2
(E)-(2R,3R,4R,7S,8S)-1,3-O-(4-methoxybenzylidene)-8-(tert-butyldimethylsilanyloxy)-2,4,6-trimethylnon-5-en-7-ol

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol0600786

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 883877-37-0
(2R,3R,4R)-3-(p-methoxybenzyloxy)-2,4-dimethyl-5-heptyn-1-ol

: 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

Guidance literature:: Multi-step reaction with 4 steps

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

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

1.3: 232 mg / DDQ / CH₂Cl₂ / 0.33 h / 0 °C

2.1: 92 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 1.5 h / 0 - 20 °C

3.1: 92 percent / DIBAL / hexane; CH₂Cl₂ / 0.17 h / -78 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; diisobutylaluminium hydride; cyclopentylmagnesium chloride; Dess-Martin periodane; triisopropoxytitanium(IV) chloride; In diethyl ether; hexane; dichloromethane; toluene; 2.1: Dess-Martin oxidation;
DOI:10.1021/ol0600786