5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole
• CAS No.: 1267597-23-8
• Molecular Formula: C₂₆H₄₆N₄O₃SSi
• Molecular Weight: 522.828

Synonyms:5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole

Chemical Property of 5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole

There total 11 articles about 5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-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: 86.0%

(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyl-decan-1-ol (1267597-22-7) + 1-Phenyl-1H-tetrazole-5-thiol (86-93-1) → 5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole (1267597-23-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201001752

Reference yield:

(4R)-5-(benzyloxy)-4-methylpentanal (1267597-10-3) → 5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole (1267597-23-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: zinc trifluoromethanesulfonate; triethylamine; N-methyl ephedrine / toluene / 1 h / 20 °C / Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere

2.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 72 h / 20 °C

4.1: triphenylphosphine; diethylazodicarboxylate / toluene / 2 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; N-methyl ephedrine; In tetrahydrofuran; dichloromethane; toluene; 4.1: Mitsunobu reaction;

DOI:10.1002/chem.201001752

Reference yield:

(4R)-5-(benzyloxy)-4-methylpentan-1-ol (1267597-08-9) → 5-[(2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole (1267597-23-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -90 °C / Inert atmosphere

1.2: 4 h / -90 - 20 °C / Inert atmosphere

2.1: zinc trifluoromethanesulfonate; triethylamine; N-methyl ephedrine / toluene / 1 h / 20 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

3.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 72 h / 20 °C

5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 2 h / 20 °C / Inert atmosphere

With oxalyl dichloride; palladium 10% on activated carbon; hydrogen; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; N-methyl ephedrine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Swern oxidation / 1.2: Swern oxidation / 5.1: Mitsunobu reaction;

DOI:10.1002/chem.201001752

upstream raw materials:

(S)-tert-butyldimethyl((5-(trimethylsilyl)pent-4-yn-2-yl)oxy)silane

(4R)-5-(benzyloxy)-4-methylpentan-1-ol

(4R)-5-(benzyloxy)-4-methylpentanal

(2R,5S,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-2-methyldec-6-yn-5-ol

Downstream raw materials:

5-((2R,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylsulfonyl)-1-phenyl-1H-tetrazole

2-bromo-1-[(3'R,6'R,10'S,E)-10-tert-butyldimethylsilyloxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-3,5-dimethoxybenzene

methyl 2-[(3R,6R,10S,E)-10-(tert-butyldimethylsilyloxy)-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate

methyl 2-[(3R,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate

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