(4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one

Base Information

Chemical Name:(4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one
CAS No.:329010-28-8
Molecular Formula:C₂₈H₃₆O₃Si
Molecular Weight:448.678
Hs Code.:

Synonyms:(4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one

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Chemical Property of (4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one

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Technology Process of (4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one

There total 13 articles about (4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-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:

: ((E)-Hex-3-enyl)-triphenyl-phosphonium; iodide

: [(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-furan-2-yl]-acetaldehyde

: 329010-28-8
(4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one

Guidance literature:: With 4 Angstroem MS; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1016/S0040-4039(00)00190-8

Reference yield:

: (E)-6-(benzyloxy)hex-3-enoic acid

: 329010-28-8
(4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: Me₃SiCl / 2 h / 20 °C

2: 90 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

3: 95 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

4: 98 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760.05 Torr

5: PCC; 4 Angstroem molecular sieves; NaOAc / CH₂Cl₂ / 2 h / 0 - 20 °C

6: 62 mg / KN(TMS)2; 4 Angstroem molecular sieves / toluene; tetrahydrofuran / 3 h / -78 °C

With 1H-imidazole; chloro-trimethyl-silane; methanesulfonamide; 4 A molecular sieve; AD-mix-β; hydrogen; sodium acetate; potassium hexamethylsilazane; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 6: Wittig reaction;
DOI:10.1021/jo0057194

Reference yield:

: 274258-70-7
methyl (E)-6-(Benzyloxy)hex-3-enoate

: 329010-28-8
(4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

2: 95 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

3: 98 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760.05 Torr

4: PCC; 4 Angstroem molecular sieves; NaOAc / CH₂Cl₂ / 2 h / 0 - 20 °C

5: 62 mg / KN(TMS)2; 4 Angstroem molecular sieves / toluene; tetrahydrofuran / 3 h / -78 °C

With 1H-imidazole; methanesulfonamide; 4 A molecular sieve; AD-mix-β; hydrogen; sodium acetate; potassium hexamethylsilazane; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 5: Wittig reaction;
DOI:10.1021/jo0057194