(3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-ol

Base Information

Chemical Name:(3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-ol
CAS No.:865487-03-2
Molecular Formula:C₂₆H₃₆O₃Si
Molecular Weight:424.656
Hs Code.:

Synonyms:(3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-ol

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Chemical Property of (3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-ol

Chemical Property:

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Technology Process of (3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-ol

There total 4 articles about (3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-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:

: 865487-02-1
(3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-dihydro-furan-2-one

: 865487-03-2
(3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2005.07.041

Reference yield:

: 54340-70-4
ethyl (E)-4-heptenoic acid ester

: 865487-03-2
(3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: CH3SO2NH2 / AD-mix-α / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C

1.2: TsOH*H₂O / CH₂Cl₂ / 1 h / 20 °C

2.1: 87 percent / imidazole / dimethylformamide / 21 h / 20 °C

3.1: 64 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

4.1: DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

With 1H-imidazole; methanesulfonamide; diisobutylaluminium hydride; lithium diisopropyl amide; AD-mix-α; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2005.07.041

Reference yield:

: 865487-01-0
(5S)-5-[(1S)-1-[tert-butyl(diphenyl)silyl]oxypropyl]tetrahydrofuran-2-one

: 865487-03-2
(3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 64 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

2: DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

With diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1016/j.tetlet.2005.07.041