5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-1-phenyl-1H-tetrazole
• CAS No.: 899798-87-9
• Molecular Formula: C₃₀H₅₆N₄O₃SSi₂
• Molecular Weight: 609.037

Synonyms:5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-1-phenyl-1H-tetrazole

Chemical Property of 5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-1-phenyl-1H-tetrazole

There total 14 articles about 5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-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: 91.0%

(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octan-1-ol (899798-81-3) + 1-Phenyl-1H-tetrazole-5-thiol (86-93-1) → 5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-1-phenyl-1H-tetrazole (899798-87-9)

Guidance literature:

With tributylphosphine; di-isopropyl azodicarboxylate; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1021/ol060669w

Reference yield:

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal (872369-17-0) → 5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-1-phenyl-1H-tetrazole (899798-87-9)

Guidance literature:

Multi-step reaction with 9 steps

1: CH₂Cl₂ / 16 h / -78 °C

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

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

4: 1,1'-carbonyl-diimidazole / CH₂Cl₂ / 16 h / 20 °C

5: 78 percent / tetrahydrofuran / 1 h / 0 °C

6: 91 percent / Me₂AlCl; Bu₃SnH / CH₂Cl₂ / 1 h / -90 °C

7: 85 percent / proton sponge / CHCl₃ / 16 h / Heating

8: 98 percent / H₂ / Pd(OH)2 / ethanol / 3 h / 20 °C

9: 91 percent / nBu₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; Proton Sponge; tributylphosphine; di-isopropyl azodicarboxylate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; dimethylaluminum chloride; 1,1'-carbonyldiimidazole; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; 1: Evans asymmetric aldolization / 9: Mitsunobu reaction;

DOI:10.1002/chem.200700342

Reference yield:

(2S,3R,4R,5S)-7-Benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide (899798-77-7) → 5-[(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octylsulfanyl]-1-phenyl-1H-tetrazole (899798-87-9)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 91 percent / Me₂AlCl; Bu₃SnH / CH₂Cl₂ / 1 h / -90 °C

3: 85 percent / proton sponge / CHCl₃ / 16 h / Heating

4: 98 percent / H₂ / Pd(OH)2 / ethanol / 3 h / 20 °C

5: 91 percent / nBu₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C

With Proton Sponge; tributylphosphine; di-isopropyl azodicarboxylate; hydrogen; tri-n-butyl-tin hydride; dimethylaluminum chloride; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; 5: Mitsunobu reaction;

DOI:10.1002/chem.200700342

upstream raw materials:

(3S,4R,5S,6R,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-octan-1-ol

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

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

(2R,3S)-5-Benzyloxy-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-pentan-1-one

Downstream raw materials:

C₄₈H₈₆O₆Si₃

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