5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-1-phenyl-1H-tetrazole
• CAS No.: 899798-88-0
• Molecular Formula: C₃₉H₇₂N₄O₅SSi₂
• Molecular Weight: 765.261
• Mol file: 899798-88-0.mol

Synonyms:5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-1-phenyl-1H-tetrazole

Chemical Property of 5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-1-phenyl-1H-tetrazole

There total 20 articles about 5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-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: 93.0%

(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-en-1-ol (899798-83-5) + 1-Phenyl-1H-tetrazole-5-thiol (86-93-1) → 5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-1-phenyl-1H-tetrazole (899798-88-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol060669w

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-1-phenyl-1H-tetrazole (899798-88-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: diisoibutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: CH₂Cl₂ / 16 h / -78 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 1 h / Heating

5.1: aq. LiOH; H₂O₂ / tetrahydrofuran / 24 h / 20 °C

6.1: 1,1'-carbonyl-diimidazole / CH₂Cl₂ / 16 h / 20 °C

7.1: 78 percent / tetrahydrofuran / 1 h / 0 °C

8.1: 91 percent / Me₂AlCl; Bu₃SnH / CH₂Cl₂ / 1 h / -90 °C

9.1: 85 percent / proton sponge / CHCl₃ / 16 h / Heating

10.1: 98 percent / H₂ / Pd(OH)2 / ethanol / 3 h / 20 °C

11.1: 91 percent / nBu₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C

12.1: 86 percent / H₂O₂ / Mo₇O₂₄(NH₄)6 / ethanol / 16 h / 20 °C

13.1: sodium hexamethyldisilazide / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / -78 °C

13.2: 75 percent / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / 2 h

14.1: 89 percent / NaOH / methanol / 4 h / Heating

15.1: 93 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium hydroxide; Proton Sponge; tributylphosphine; di-isopropyl azodicarboxylate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; dimethylaluminum chloride; triphenylphosphine; 1,1'-carbonyldiimidazole; palladium dihydroxide; ammonium molybdate tetrahydrate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; chloroform; 3.1: Evans asymmetric aldolization / 11.1: Mitsunobu reaction / 13.1: Julia-Kocienski olefination / 13.2: Julia-Kociensky olefination / 15.1: Mitsunobu reaction;

DOI:10.1002/chem.200700342

Reference yield:

[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octyloxymethyl]-benzene (899798-80-2) → 5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-enylsulfanyl]-1-phenyl-1H-tetrazole (899798-88-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / H₂ / Pd(OH)2 / ethanol / 3 h / 20 °C

2.1: 91 percent / nBu₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C

3.1: 86 percent / H₂O₂ / Mo₇O₂₄(NH₄)6 / ethanol / 16 h / 20 °C

4.1: sodium hexamethyldisilazide / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / -78 °C

4.2: 75 percent / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / 2 h

5.1: 89 percent / NaOH / methanol / 4 h / Heating

6.1: 93 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C

With sodium hydroxide; tributylphosphine; di-isopropyl azodicarboxylate; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; triphenylphosphine; palladium dihydroxide; ammonium molybdate tetrahydrate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; ethanol; 2.1: Mitsunobu reaction / 4.1: Julia-Kocienski olefination / 4.2: Julia-Kociensky olefination / 6.1: Mitsunobu reaction;

DOI:10.1002/chem.200700342

upstream raw materials:

(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-en-1-ol

1-Phenyl-1H-tetrazole-5-thiol

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

(2S,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentan-1-ol

Downstream raw materials:

5-[(E)-(3S,4S,9S,10R,11S,12R,13S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methoxy-3-methoxymethoxy-4,10,12-trimethyl-tetradec-6-ene-1-sulfonyl]-1-phenyl-1H-tetrazole