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

Base Information

Chemical Name:(3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-dihydro-furan-2-one
CAS No.:865487-02-1
Molecular Formula:C₂₆H₃₄O₃Si
Molecular Weight:422.64
Hs Code.:

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

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

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

There total 4 articles about (3R,5S)-3-Allyl-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-propyl]-dihydro-furan-2-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: 64.0%

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

: 106-95-6
allyl bromide

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

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2005.07.041

Reference yield: 64.0%

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

: 106-95-6
allyl bromide

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

: C₂₆H₃₄O₃Si

Guidance literature:: (5S)-5-[(1S)-1-[tert-butyl(diphenyl)silyl]oxypropyl]tetrahydrofuran-2-one; With lithium diisopropyl amide;

allyl bromide; Further stages.;
DOI:10.1271/bbb.80173

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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