5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole
• CAS No.: 591770-19-3
• Molecular Formula: C₂₅H₄₆N₄O₂SSi₂
• Molecular Weight: 522.903
• Mol file: 591770-19-3.mol

Synonyms:5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole

Chemical Property of 5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole

There total 12 articles about 5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-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: 84.0%

1-Phenyl-1H-tetrazole-5-thiol (86-93-1) + (2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methyl-1-pentanol (188926-24-1) → 5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole (591770-19-3)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200210695

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole (591770-19-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / 2,6-lutidine / CH₂Cl₂

2.1: 75 percent / NaBH₄ / H₂O; tetrahydrofuran

3.1: 95 percent / pyridine / 2 h / 0 °C

4.1: 95 percent / NaI; DBU / various solvent(s) / 3 h / Heating

5.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C

5.2: 83 percent / NaOH; H₂O₂ / ethanol; tetrahydrofuran / 2 h / 20 °C

6.1: 84 percent / diisopropyl azodicarboxylate; triphenylphosphane / dimethylformamide / 0.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; di-isopropyl azodicarboxylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; sodium iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200210695

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → 5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole (591770-19-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: titanium(IV) chloride; (-)-sparteine / CH₂Cl₂ / 0.33 h / 0 °C

1.2: 87 percent / CH₂Cl₂ / 1 h / 0 °C

2.1: 93 percent / 2,6-lutidine / CH₂Cl₂

3.1: 75 percent / NaBH₄ / H₂O; tetrahydrofuran

4.1: 95 percent / pyridine / 2 h / 0 °C

5.1: 95 percent / NaI; DBU / various solvent(s) / 3 h / Heating

6.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C

6.2: 83 percent / NaOH; H₂O₂ / ethanol; tetrahydrofuran / 2 h / 20 °C

7.1: 84 percent / diisopropyl azodicarboxylate; triphenylphosphane / dimethylformamide / 0.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; di-isopropyl azodicarboxylate; titanium tetrachloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; sodium iodide; (-)-sparteine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200210695

upstream raw materials:

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

(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methyl-1-pentanol

t-butyldimethylsiyl triflate

3-(tert-butyldimethylsilanyloxy)propionaldehyde

Downstream raw materials:

{(1E,3R,4S)-4,6-bis{[(tert-butyl)dimethylsilyl]oxy}-3-methylhex-1-enyl}benzene

(3S,4R,5E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-6-phenylhex-5-en-1-ol

(3S,4R,5E)-3-[(tert-butyldimethylsilyl)oxy]-4-methyl-6-phenyl-5-hexenal

5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfonyl}-1-phenyl-1H-tetrazole