(+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

Base Information

Chemical Name:(+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one
CAS No.:1370254-21-9
Molecular Formula:C₂₂H₃₆O₃Si
Molecular Weight:376.612
Hs Code.:

Synonyms:(+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

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Chemical Property of (+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

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Technology Process of (+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

There total 9 articles about (+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-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: 80.0%

: 1370254-18-4
dimethyl (-)-(R)-4-(benzyloxy)-3-methyl-2-oxobutylphosphonate

: 104701-87-3
(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

: 1370254-21-9
(+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

Guidance literature:: dimethyl (-)-(R)-4-(benzyloxy)-3-methyl-2-oxobutylphosphonate; With lithium hydroxide monohydrate; In tetrahydrofuran; at 0 ℃; for 0.166667h; Inert atmosphere;

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1055/s-0031-1289661

Reference yield: 70.0%

: 1421359-36-5
(2S,3S,6R)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-oxoheptan-3-yl 2-(diethoxyphosphoryl)acetate

: 1370254-21-9
(+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

: 1421359-34-3
(S)-4-((S)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-5,6-dihydropyran-2-one

Guidance literature:: With lithium tert-butoxide; In tetrahydrofuran; at 30 - 40 ℃; for 0.25h; Reagent/catalyst; Temperature; Concentration;
DOI:10.1021/jo302440a

Reference yield:

: 56850-58-9,59965-24-1,74924-27-9,112068-34-5
methyl (2R)-3-(benzyloxy)-2-methylpropanoate

: 1370254-21-9
(+)-(2R,6R,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

With n-butyllithium; lithium hydroxide monohydrate; In tetrahydrofuran; hexane; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1289661