5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-1-phenyl-1H-tetrazole
• CAS No.: 1333237-57-2
• Molecular Formula: C₃₄H₄₁Cl₃N₄O₃SSi
• Molecular Weight: 720.235

Synonyms:5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-1-phenyl-1H-tetrazole

Chemical Property of 5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-1-phenyl-1H-tetrazole

There total 15 articles about 5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-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: 72.0%

((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methanol (1333237-56-1) + 1-Phenyl-1H-tetrazole-5-thiol (86-93-1) → 5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-1-phenyl-1H-tetrazole (1333237-57-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 1.75h; Inert atmosphere;

DOI:10.1002/anie.201102521

Reference yield:

C25H35Cl2NOSi → 5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-1-phenyl-1H-tetrazole (1333237-57-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrogenchloride; water / 3 h / 20 °C / Inert atmosphere

2.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 20 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

2.3: 0.5 h / 20 °C / Inert atmosphere

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / -78 - 20 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium / nonane; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: zirconium(IV) chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

6.2: 0.08 h / 0 - 20 °C / Inert atmosphere

7.1: sodium tetrahydroborate / methanol / 1.33 h / -78 °C / Inert atmosphere

7.2: 0.17 h / -78 - 20 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / dichloromethane / 24.67 h / 0 - 20 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C

10.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.75 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; bis(acetylacetonate)oxovanadium; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; (-)-N-methylephedrine; water; hydrogen; pyridinium p-toluenesulfonate; zirconium(IV) chloride; zinc trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; nonane; dichloromethane; ethyl acetate; toluene; 5.1: Dess-Martin oxidation / 10.1: Mitsunobu reaction;

DOI:10.1002/anie.201102521

Reference yield:

C25H37NOSi → 5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylthio)-1-phenyl-1H-tetrazole (1333237-57-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: N-chloro-succinimide / tetrachloromethane; dichloromethane / 24.17 h / 0 - 20 °C / Darkness; Inert atmosphere

2.1: hydrogenchloride; water / 3 h / 20 °C / Inert atmosphere

3.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 20 °C / Inert atmosphere

3.2: 18 h / 20 °C / Inert atmosphere

3.3: 0.5 h / 20 °C / Inert atmosphere

4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / -78 - 20 °C / Inert atmosphere

4.2: -78 °C / Inert atmosphere

5.1: tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium / nonane; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

7.1: zirconium(IV) chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

7.2: 0.08 h / 0 - 20 °C / Inert atmosphere

8.1: sodium tetrahydroborate / methanol / 1.33 h / -78 °C / Inert atmosphere

8.2: 0.17 h / -78 - 20 °C / Inert atmosphere

9.1: pyridinium p-toluenesulfonate / dichloromethane / 24.67 h / 0 - 20 °C / Inert atmosphere

10.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C

11.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.75 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; N-chloro-succinimide; bis(acetylacetonate)oxovanadium; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; (-)-N-methylephedrine; water; hydrogen; pyridinium p-toluenesulfonate; zirconium(IV) chloride; zinc trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; tetrachloromethane; nonane; dichloromethane; ethyl acetate; toluene; 6.1: Dess-Martin oxidation / 11.1: Mitsunobu reaction;

DOI:10.1002/anie.201102521

upstream raw materials:

(R)-1-(benzyloxy)-8-(tert-butyldiphenylsilyloxy)-5,5-dichlorooct-2-yn-4-ol

(R,e)-1-(benzyloxy)-8-(tert-butyldiphenylsilyloxy)-5,5-dichlorooct-2-en-4-ol

(R)-1-((2S,3S)-3-(benzyloxymethyl)oxiran-2-yl)-5-(tert-butyldiphenylsilyloxy)-2,2-dichloropentan-1-ol

1-((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)-5-((tert-butyldiphenylsilyl)oxy)-2,2-dichloropentan-1-one

Downstream raw materials:

5-(((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)methylsulfonyl)-1-phenyl-1H-tetrazole

(Z)-tert-butyl(4,4-dichloro-4-((4R,5S,6S)-5-chloro-6-((Z)-2-((2S,3S)-3-((1R,2S)-1,2-dichloro-3-((S)-2,2-di-methyl-1,3-dioxolan-4-yl)propyl)oxiran-2-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)butoxy)diphenylsilane

(3R,4S,5R,6S,Z)-1-((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-di-methyl-1,3-dioxan-4-yl)-3,5,6-trichloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol

(1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol

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