(S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

Base Information

Chemical Name:(S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one
CAS No.:440677-16-7
Molecular Formula:C₄₉H₇₄O₅Si₂
Molecular Weight:799.295
Hs Code.:

(S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

Synonyms:(S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

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Chemical Property of (S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

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Technology Process of (S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

There total 10 articles about (S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-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: 98.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 440677-15-6
(S)-5-{(2E,4E)-(S)-6-Hydroxy-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

: 440677-16-7
(S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

Guidance literature:: With 1H-imidazole; In dichloromethane; at 25 ℃; for 12h;
DOI:10.1055/s-2002-20450

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 440677-16-7
(S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / imidazole / CH₂Cl₂ / 5 h / 0 - 25 °C

2.1: 9-BBN / tetrahydrofuran / 12 h / 25 °C

2.2: 94 percent / NaOH; aq. H₂O₂ / 2 h / 0 °C

3.1: 98 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 25 °C

4.1: t-BuLi / tetrahydrofuran / 0.5 h / -78 °C

4.2: tetrahydrofuran / 0.33 h

5.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 25 °C

6.1: 90 percent / LiCl; i-Pr₂NEt / acetonitrile / 2 h / 0 °C

7.1: 98 percent / (R)-B-Me-CBS; BMS / toluene / 0.17 h / -10 °C

8.1: 98 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; dimethylsulfide borane complex; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; (R)-(+)-tetrahydro-1-methyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 6.1: Horner-Wadsworth-Emmons reaction / 7.1: Corey-Bakshi-Shibata asymmetric reduction;
DOI:10.1055/s-2002-20450

Reference yield:

: 440677-08-7
(E)-3-((2R,3R,5R)-5-Allyl-3-methyl-tetrahydro-furan-2-yl)-but-2-en-1-ol

: 440677-16-7
(S)-5-{(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-1-methylene-8-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-octa-2,4-dienyl}-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / imidazole / CH₂Cl₂ / 5 h / 0 - 25 °C

2.1: 9-BBN / tetrahydrofuran / 12 h / 25 °C

2.2: 94 percent / NaOH; aq. H₂O₂ / 2 h / 0 °C

3.1: 98 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 25 °C

4.1: t-BuLi / tetrahydrofuran / 0.5 h / -78 °C

4.2: tetrahydrofuran / 0.33 h

5.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 25 °C

6.1: 90 percent / LiCl; i-Pr₂NEt / acetonitrile / 2 h / 0 °C

7.1: 98 percent / (R)-B-Me-CBS; BMS / toluene / 0.17 h / -10 °C

8.1: 98 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; dimethylsulfide borane complex; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; (R)-(+)-tetrahydro-1-methyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 6.1: Horner-Wadsworth-Emmons reaction / 7.1: Corey-Bakshi-Shibata asymmetric reduction;
DOI:10.1055/s-2002-20450