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

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Chemical Name:(3S,4R,5E,10R)-1,1-dibromo-5-(t-butyldimethylsilyloxy)methyl-10-(t-butyldiphenylsilyloxy)-4-methoxymethoxy-3-methylundeca-1,5-diene
CAS No.:854612-99-0
Molecular Formula:C₃₇H₅₈Br₂O₄Si₂
Molecular Weight:782.844
Hs Code.:

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

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Chemical Property of (3S,4R,5E,10R)-1,1-dibromo-5-(t-butyldimethylsilyloxy)methyl-10-(t-butyldiphenylsilyloxy)-4-methoxymethoxy-3-methylundeca-1,5-diene

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Technology Process of (3S,4R,5E,10R)-1,1-dibromo-5-(t-butyldimethylsilyloxy)methyl-10-(t-butyldiphenylsilyloxy)-4-methoxymethoxy-3-methylundeca-1,5-diene

There total 17 articles about (3S,4R,5E,10R)-1,1-dibromo-5-(t-butyldimethylsilyloxy)methyl-10-(t-butyldiphenylsilyloxy)-4-methoxymethoxy-3-methylundeca-1,5-diene 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:

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

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

Guidance literature:: Multi-step reaction with 17 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

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; 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

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

Guidance literature:: Multi-step reaction with 15 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

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; 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

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

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

Guidance literature:: Multi-step reaction with 18 steps

1.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 22 h / 0 °C

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

3.1: 30.0 g / LiCl; DBU / acetonitrile / 1 h

4.1: H₂ / Pd/C / ethanol / 23 h

5.1: 21.0 g / DIBAL-H / CH₂Cl₂; toluene / 2 h / -18 °C

6.1: 100 percent / PPh₃; I₂; imidazole / acetonitrile; tetrahydrofuran / 1 h / 0 °C

7.1: 95 percent / dimethylsulfoxide / 5.5 h / 0 °C

8.1: DIBAL-H / toluene / 2 h / -78 °C

8.2: 95 percent / HCl; NH₄Cl / H₂O / -78 - 20 °C

9.1: 86 percent / DABCO / methanol / 120 h

10.1: 95 percent / NBS; Me₂S / CH₂Cl₂ / 6 h / 0 °C

11.1: 81 percent / Na₂HPO₄; NaH₂PO₄ / CH₂Cl₂; various solvent(s) / 7 h / 100 °C

12.1: 93 percent / imidazole / dimethylformamide / 1 h / 0 °C

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

14.1: 1.25 g / MnO₂ / CH₂Cl₂ / 0.17 h / 0 °C

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

15.2: CH₂Cl₂ / 5 h / -78 - 0 °C

15.3: 84 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / Heating

16.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 27 h / 0 °C

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

18.1: 602 mg / PPh₃; Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-Bromosuccinimide; dimethylsulfide; di-n-butylboryl trifluoromethanesulfonate; 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; 3.1: Horner-Emmons olefination / 9.1: Morita-Baylis-Hillman reaction / 18.1: Corey-Fuchs dibromoolefination;
DOI:10.1021/ol050763x