(+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

Base Information

Chemical Name:(+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal
CAS No.:1370254-30-0
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

Synonyms:(+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

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Chemical Property of (+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

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Technology Process of (+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

There total 7 articles about (+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal 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: 98.0%

: 1370254-50-4
(-)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-1-ol

: 1370254-30-0
(+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h; 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

: 1370254-30-0
(+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

Guidance literature:: Multi-step reaction with 7 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

4.1: pyridine; palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

6.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; n-butyllithium; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1289661

Reference yield:

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

: 1370254-30-0
(+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 18 h / 20 °C / Inert atmosphere

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

2.2: -40 °C / Inert atmosphere

3.1: pyridine; palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

5.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1289661