(2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester
• CAS No.: 190438-30-3
• Molecular Formula: C₅₂H₉₃NO₅Si₃
• Molecular Weight: 896.571

Synonyms:

Chemical Property of (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

There total 10 articles about (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester 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:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester (190438-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) imidazole, 2.) NaH / 1.) DMF, 2.) THF

2: pyridine

3: NaH / tetrahydrofuran

With 1H-imidazole; sodium hydride; In tetrahydrofuran; pyridine;

DOI:10.1016/S0040-4039(97)00603-5

Reference yield:

(3aS,4S,6aS)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate (178456-74-1) → (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester (190438-30-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) BuLi, 2.) NaBH₄ / 1.) THF, -78 deg C, 2.) EtOH

2: 98 percent / tetrahydrofuran / 40 °C

3: 70 percent / Bu₃SnH, AIBN / toluene / 95 °C

4: 63 percent / p-TsOH / methanol

5: 75 percent / Et₃N / CH₂Cl₂

6: 1.) imidazole, 2.) NaH / 1.) DMF, 2.) THF

7: pyridine

8: NaH / tetrahydrofuran

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4039(97)00603-5

Reference yield:

tert-Butyl-((S)-1-isobutyl-dec-9-ynyloxy)-dimethyl-silane → (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester (190438-30-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) BuLi, 2.) NaBH₄ / 1.) THF, -78 deg C, 2.) EtOH

2: 98 percent / tetrahydrofuran / 40 °C

3: 70 percent / Bu₃SnH, AIBN / toluene / 95 °C

4: 63 percent / p-TsOH / methanol

5: 75 percent / Et₃N / CH₂Cl₂

6: 1.) imidazole, 2.) NaH / 1.) DMF, 2.) THF

7: pyridine

8: NaH / tetrahydrofuran

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4039(97)00603-5

upstream raw materials:

tert-butyldimethylsilyl chloride

(3aS,4S,6aS)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

((S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-{(4S,5R)-5-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-13-methyl-tetradecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-carbamic acid tert-butyl ester

((S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-{(4S,5R)-5-[(S)-11-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-13-methyl-tetradec-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-carbamic acid tert-butyl ester

Downstream raw materials:

penaresidin B

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