(3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne

Base Information

Chemical Name:(3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne
CAS No.:854613-00-6
Molecular Formula:C₃₁H₄₃BrO₄Si
Molecular Weight:587.67
Hs Code.:

Synonyms:(3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne

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Chemical Property of (3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne

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Technology Process of (3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne

There total 18 articles about (3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne 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: 89.0%

: 854612-99-0
(3S,4R,5E,10R)-1,1-dibromo-5-(t-butyldimethylsilyloxy)methyl-10-(t-butyldiphenylsilyloxy)-4-methoxymethoxy-3-methylundeca-1,5-diene

: 854613-00-6
(3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 4h;
DOI:10.1021/ol050763x

Reference yield:

: 561038-05-9
(R)-2-(tert-butyldiphenylsilanyloxy)propionic acid methyl ester

: 854613-00-6
(3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne

Guidance literature:: Multi-step reaction with 18 steps

1.1: DIBAL-H / toluene / 1.5 h / -78 °C

2.1: 30.0 g / LiCl; DBU / acetonitrile / 1 h

3.1: H₂ / Pd/C / ethanol / 23 h

4.1: 21.0 g / DIBAL-H / CH₂Cl₂; toluene / 2 h / -18 °C

5.1: 100 percent / PPh₃; I₂; imidazole / acetonitrile; tetrahydrofuran / 1 h / 0 °C

6.1: 95 percent / dimethylsulfoxide / 5.5 h / 0 °C

7.1: DIBAL-H / toluene / 2 h / -78 °C

7.2: 95 percent / HCl; NH₄Cl / H₂O / -78 - 20 °C

8.1: 86 percent / DABCO / methanol / 120 h

9.1: 95 percent / NBS; Me₂S / CH₂Cl₂ / 6 h / 0 °C

10.1: 81 percent / Na₂HPO₄; NaH₂PO₄ / CH₂Cl₂; various solvent(s) / 7 h / 100 °C

11.1: 93 percent / imidazole / dimethylformamide / 1 h / 0 °C

12.1: DIBAL-H / toluene; CH₂Cl₂ / 2 h / -78 °C

13.1: 1.25 g / MnO₂ / CH₂Cl₂ / 0.17 h / 0 °C

14.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

14.2: CH₂Cl₂ / 5 h / -78 - 0 °C

14.3: 84 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / Heating

15.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 27 h / 0 °C

16.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

17.1: 602 mg / PPh₃; Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

18.1: 89 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 4 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-Bromosuccinimide; dimethylsulfide; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Horner-Emmons olefination / 8.1: Morita-Baylis-Hillman reaction / 17.1: Corey-Fuchs dibromoolefination;
DOI:10.1021/ol050763x

Reference yield:

: 854612-89-8
ethyl (2E,4R)-4-(t-butyldiphenylsilyloxy)-2-pentenoate

: 854613-00-6
(3S,4R,5E,10R)-1-bromo-10-(t-butyldiphenylsilyloxy)-5-hydroxymethyl-4-methoxymethoxy-3-methylundec-5-en-1-yne

Guidance literature:: Multi-step reaction with 16 steps

1.1: H₂ / Pd/C / ethanol / 23 h

2.1: 21.0 g / DIBAL-H / CH₂Cl₂; toluene / 2 h / -18 °C

3.1: 100 percent / PPh₃; I₂; imidazole / acetonitrile; tetrahydrofuran / 1 h / 0 °C

4.1: 95 percent / dimethylsulfoxide / 5.5 h / 0 °C

5.1: DIBAL-H / toluene / 2 h / -78 °C

5.2: 95 percent / HCl; NH₄Cl / H₂O / -78 - 20 °C

6.1: 86 percent / DABCO / methanol / 120 h

7.1: 95 percent / NBS; Me₂S / CH₂Cl₂ / 6 h / 0 °C

8.1: 81 percent / Na₂HPO₄; NaH₂PO₄ / CH₂Cl₂; various solvent(s) / 7 h / 100 °C

9.1: 93 percent / imidazole / dimethylformamide / 1 h / 0 °C

10.1: DIBAL-H / toluene; CH₂Cl₂ / 2 h / -78 °C

11.1: 1.25 g / MnO₂ / CH₂Cl₂ / 0.17 h / 0 °C

12.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

12.2: CH₂Cl₂ / 5 h / -78 - 0 °C

12.3: 84 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / Heating

13.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 27 h / 0 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

15.1: 602 mg / PPh₃; Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

16.1: 89 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 4 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-Bromosuccinimide; dimethylsulfide; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Morita-Baylis-Hillman reaction / 15.1: Corey-Fuchs dibromoolefination;
DOI:10.1021/ol050763x