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

Base Information

Chemical Name:(-)-(2R,3S,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-ol
CAS No.:1370254-22-0
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

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

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

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

There total 4 articles about (-)-(2R,3S,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-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: 86.0%

: 1370254-20-8
(-)-(2R,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

: 1370254-22-0
(-)-(2R,3S,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-ol

Guidance literature:: (-)-(2R,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one; With (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -40 ℃; for 1h; Inert atmosphere;

With borane-THF; In tetrahydrofuran; toluene; at -40 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0031-1289661

Reference yield:

: 1370254-20-8
(-)-(2R,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one

: 1370254-22-0
(-)-(2R,3S,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-ol

: 1370254-23-1
(-)-(2R,3R,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-ol

Guidance literature:: (-)-(2R,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-one; With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -40 ℃; for 1h; Inert atmosphere;

With borane-THF; In tetrahydrofuran; toluene; at -40 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0031-1289661

Reference yield:

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

: 1370254-22-0
(-)-(2R,3S,6S,E)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-en-3-ol

Guidance literature:: Multi-step reaction with 3 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

3.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1 h / -40 °C / Inert atmosphere

3.2: -40 °C / Inert atmosphere

With n-butyllithium; lithium hydroxide monohydrate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; toluene; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1289661