(+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol

Base Information

Chemical Name:(+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol
CAS No.:1370254-47-9
Molecular Formula:C₂₂H₄₀O₃Si
Molecular Weight:380.643
Hs Code.:

Synonyms:(+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol

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Chemical Property of (+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol

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Technology Process of (+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol

There total 5 articles about (+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-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: 87.0%

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

: 1370254-47-9
(+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol

Guidance literature:: With pyridine; palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; Inert atmosphere;
DOI:10.1055/s-0031-1289661

Reference yield:

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

: 1370254-47-9
(+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 18 h / 20 °C / Inert atmosphere

2.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[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

With pyridine; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; toluene; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;
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

: 1370254-47-9
(+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1 h / -40 °C / Inert atmosphere

1.2: -40 °C / Inert atmosphere

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

With pyridine; palladium 10% on activated carbon; hydrogen; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; toluene;
DOI:10.1055/s-0031-1289661