5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole
• CAS No.: 925231-82-9
• Molecular Formula: C₃₈H₆₂N₄O₄SSi
• Molecular Weight: 699.086

Synonyms:5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole

Chemical Property of 5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole

There total 14 articles about 5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole 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:

hydroxy-[2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid ethyl ester (925231-64-7) → 5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole (925231-82-9)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 95 percent / 4-(dimethylamino)pyridine; ethyldiisopropylamine / CH₂Cl₂ / 10 h / Heating

2.1: 75 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 2 h / -78 °C

3.1: molecular sieves 4 Angstroem / toluene / 36 h / -78 °C

3.2: aq. NaOH / toluene / 1 h / 0 °C

4.1: 99 percent / collidine / CH₂Cl₂ / 2 h / 20 °C

5.1: 92 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 2 h / 0 °C

6.1: 99 percent / Et₃N / CH₂Cl₂ / 6 h / 0 °C

7.1: 96 percent / N-methylmorpholine / CH₂Cl₂ / 12 h

8.1: 93 percent / NaI / acetone / 3 h / Heating

9.1: 92 percent / tris(trimethylsilyl)silane; triethylborane / toluene / 1 h / -20 °C

10.1: 2-methyl-2-butene; disiamylborane / tetrahydrofuran; hexane / 3 h / 0 °C

10.2: 92 percent / sodium perborate tetrahydrate / tetrahydrofuran; hexane / 1 h / 20 °C

11.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

12.1: 95 percent / Cs₂CO₃ / ethanol / 1 h / 20 °C

13.1: second generation Grubbs catalyst / CH₂Cl₂ / 3 h / 20 °C

14.1: 102 mg / second generation Grubbs catalyst / CH₂Cl₂ / 24 h / 40 °C

15.1: 96 percent / diisobutylaluminum hydride / toluene; tetrahydrofuran / 1 h / -78 °C

16.1: potassium t-butoxide / tetrahydrofuran / 0.17 h / 0 °C

16.2: tetrahydrofuran / 0.33 h / 0 - 20 °C

17.1: 189 mg / mercury(II) acetate; H₂O / tetrahydrofuran / 0.5 h / 0 °C

18.1: 92 percent / sodium borohydride / methanol / 0.5 h / 20 °C

19.1: 94 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / 20 °C

With 4-methyl-morpholine; pyridine; 2,3,5-trimethyl-pyridine; dmap; sodium tetrahydroborate; 2-methyl-but-2-ene; ammonium cerium(IV) nitrate; triethyl borane; di-isopropyl azodicarboxylate; tris-(trimethylsilyl)silane; 4 A molecular sieve; potassium tert-butylate; mercury(II) diacetate; water; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; 3.1: Roush crotylation / 16.2: Wittig reaction;

DOI:10.1002/anie.200603363

Reference yield:

methoxymethoxy-[2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid ethyl ester (925231-65-8) → 5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole (925231-82-9)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 75 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 2 h / -78 °C

2.1: molecular sieves 4 Angstroem / toluene / 36 h / -78 °C

2.2: aq. NaOH / toluene / 1 h / 0 °C

3.1: 99 percent / collidine / CH₂Cl₂ / 2 h / 20 °C

4.1: 92 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 2 h / 0 °C

5.1: 99 percent / Et₃N / CH₂Cl₂ / 6 h / 0 °C

6.1: 96 percent / N-methylmorpholine / CH₂Cl₂ / 12 h

7.1: 93 percent / NaI / acetone / 3 h / Heating

8.1: 92 percent / tris(trimethylsilyl)silane; triethylborane / toluene / 1 h / -20 °C

9.1: 2-methyl-2-butene; disiamylborane / tetrahydrofuran; hexane / 3 h / 0 °C

9.2: 92 percent / sodium perborate tetrahydrate / tetrahydrofuran; hexane / 1 h / 20 °C

10.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

11.1: 95 percent / Cs₂CO₃ / ethanol / 1 h / 20 °C

12.1: second generation Grubbs catalyst / CH₂Cl₂ / 3 h / 20 °C

13.1: 102 mg / second generation Grubbs catalyst / CH₂Cl₂ / 24 h / 40 °C

14.1: 96 percent / diisobutylaluminum hydride / toluene; tetrahydrofuran / 1 h / -78 °C

15.1: potassium t-butoxide / tetrahydrofuran / 0.17 h / 0 °C

15.2: tetrahydrofuran / 0.33 h / 0 - 20 °C

16.1: 189 mg / mercury(II) acetate; H₂O / tetrahydrofuran / 0.5 h / 0 °C

17.1: 92 percent / sodium borohydride / methanol / 0.5 h / 20 °C

18.1: 94 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / 20 °C

With 4-methyl-morpholine; pyridine; 2,3,5-trimethyl-pyridine; sodium tetrahydroborate; 2-methyl-but-2-ene; ammonium cerium(IV) nitrate; triethyl borane; di-isopropyl azodicarboxylate; tris-(trimethylsilyl)silane; 4 A molecular sieve; potassium tert-butylate; mercury(II) diacetate; water; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; sodium iodide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; 2.1: Roush crotylation / 15.2: Wittig reaction;

DOI:10.1002/anie.200603363

Reference yield:

[5-(1-methoxymethoxy-3-methyl-2-triisopropylsilanyloxy-pent-4-enyl)-tetrahydro-furan-2-yl]-acetic acid ethyl ester (925231-73-8) → 5-{3-[5-(1-methoxymethoxy-3,9-dimethyl-5-methylene-2-triisopropylsilanyloxy-deca-6,9-dienyl)-tetrahydro-furan-2-yl]-propylsulfanyl}-1-phenyl-1H-tetrazole (925231-82-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 2-methyl-2-butene; disiamylborane / tetrahydrofuran; hexane / 3 h / 0 °C

1.2: 92 percent / sodium perborate tetrahydrate / tetrahydrofuran; hexane / 1 h / 20 °C

2.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

3.1: 95 percent / Cs₂CO₃ / ethanol / 1 h / 20 °C

4.1: second generation Grubbs catalyst / CH₂Cl₂ / 3 h / 20 °C

5.1: 102 mg / second generation Grubbs catalyst / CH₂Cl₂ / 24 h / 40 °C

6.1: 96 percent / diisobutylaluminum hydride / toluene; tetrahydrofuran / 1 h / -78 °C

7.1: potassium t-butoxide / tetrahydrofuran / 0.17 h / 0 °C

7.2: tetrahydrofuran / 0.33 h / 0 - 20 °C

8.1: 189 mg / mercury(II) acetate; H₂O / tetrahydrofuran / 0.5 h / 0 °C

9.1: 92 percent / sodium borohydride / methanol / 0.5 h / 20 °C

10.1: 94 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / 20 °C

With pyridine; sodium tetrahydroborate; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; potassium tert-butylate; mercury(II) diacetate; water; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; triphenylphosphine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; 7.2: Wittig reaction;

DOI:10.1002/anie.200603363

upstream raw materials:

methoxymethoxy-[2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetaldehyde

hydroxy-[2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid ethyl ester

methoxymethoxy-[2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid ethyl ester

[5-(1-methoxymethoxy-3-methyl-2-triisopropylsilanyloxy-pent-4-enyl)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

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