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

Base Information

Chemical Name:(E)-(2R,3R,4R,8S)-1,8-di(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-2,4,6-trimethylnon-5-en-7-one
CAS No.:883877-39-2
Molecular Formula:C₃₂H₅₈O₅Si₂
Molecular Weight:578.981
Hs Code.:

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

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

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

There total 1 articles about (E)-(2R,3R,4R,8S)-1,8-di(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-2,4,6-trimethylnon-5-en-7-one 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: 91.0%

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

: 883877-39-2
(E)-(2R,3R,4R,8S)-1,8-di(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-2,4,6-trimethylnon-5-en-7-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol0600786

Reference yield:

: 883877-39-2
(E)-(2R,3R,4R,8S)-1,8-di(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-2,4,6-trimethylnon-5-en-7-one

: (E)-(2S,3S,4R,7R,8R,9R,12S,13S)-13-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-5-eth-(E)-ylidene-3,8-bis-(4-methoxy-benzyloxy)-2,4,7,9,11-pentamethyl-12-triisopropylsilanyloxy-tetradec-10-en-6-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: DIBAL / hexane / 0.17 h / -78 °C

1.2: 237 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2.1: 79 percent / pyridine*HF; pyridine / tetrahydrofuran / 2 h / 20 °C

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

4.1: c-C₅H₉MgCl / Ti(OiPr)3Cl / toluene; hexane; diethyl ether / 2 h / -40 °C

4.2: BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

With pyridine; diisobutylaluminium hydride; cyclopentylmagnesium chloride; Dess-Martin periodane; pyridine hydrogenfluoride; triisopropoxytitanium(IV) chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 3.1: Dess-Martin oxidation;
DOI:10.1021/ol0600786

Reference yield:

: 883877-39-2
(E)-(2R,3R,4R,8S)-1,8-di(tert-butyldimethylsilanyloxy)-3-(p-methoxybenzyloxy)-2,4,6-trimethylnon-5-en-7-one

: (E,E)-(2S,3S,4R,7R,8R,9R,10R,13S,14S)-1-(tert-butyldiphenylsilanyloxy)-3,9-di(p-methoxybenzyloxy)-13-(tri-isopropylsilanyloxy)-14-(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylpentadeca-5,11-dien-7-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: DIBAL / hexane / 0.17 h / -78 °C

1.2: 237 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2.1: 79 percent / pyridine*HF; pyridine / tetrahydrofuran / 2 h / 20 °C

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

4.1: c-C₅H₉MgCl / Ti(OiPr)3Cl / toluene; hexane; diethyl ether / 2 h / -40 °C

4.2: BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C

With pyridine; diisobutylaluminium hydride; cyclopentylmagnesium chloride; Dess-Martin periodane; pyridine hydrogenfluoride; triisopropoxytitanium(IV) chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 3.1: Dess-Martin oxidation;
DOI:10.1021/ol0600786