(S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate

Base Information

• Chemical Name: (S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate
• CAS No.: 1466431-01-5
• Molecular Formula: C₂₅H₃₉NO₆Si
• Molecular Weight: 477.673
• Mol file: 1466431-01-5.mol

Synonyms:(S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate

Chemical Property of (S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate

There total 7 articles about (S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate 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: 73.0%

C25H41NO6Si (1466431-00-4) → (S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate (1466431-01-5)

Guidance literature:

With Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0033-1338493

Reference yield:

(S)-tert-butyl(1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-yloxy)dimethylsilane (1414941-22-2) → (S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate (1466431-01-5)

Guidance literature:

Multi-step reaction with 5 steps

1: ozone; triphenylphosphine / dichloromethane / -78 - 20 °C

2: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tert-butyl alcohol; water / 1.5 h / 20 °C / Inert atmosphere

3: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -30 - 20 °C / Inert atmosphere

4: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C / Inert atmosphere

5: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / -78 - 20 °C / Inert atmosphere

With 4-methyl-morpholine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Bromotrichloromethane; diethylamino-sulfur trifluoride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1055/s-0033-1338493

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate (1466431-01-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: ozone; triphenylphosphine / dichloromethane / -78 - 20 °C

3: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tert-butyl alcohol; water / 1.5 h / 20 °C / Inert atmosphere

4: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -30 - 20 °C / Inert atmosphere

5: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C / Inert atmosphere

6: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / -78 - 20 °C / Inert atmosphere

With 4-methyl-morpholine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Bromotrichloromethane; diethylamino-sulfur trifluoride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1055/s-0033-1338493

upstream raw materials:

(S)-tert-butyl(1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-yloxy)dimethylsilane

(S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-4,4-dimethylpentanoic acid

t-butyldimethylsiyl triflate

(S)-1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-ol

Downstream raw materials:

(2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one

(2S,5R,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one

(2S,6S,7S)-2-[(tert-Butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-one

(2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol