(S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide

Base Information

• Chemical Name: (S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide
• CAS No.: 1337973-23-5
• Molecular Formula: C₂₁H₃₇NO₆Si
• Molecular Weight: 427.613

Synonyms:(S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide

Chemical Property of (S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide

There total 6 articles about (S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide 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: 81.0%

(S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)propanoic acid (1337973-15-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide (1337973-23-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 10h; Inert atmosphere;

DOI:10.1007/s12272-011-0805-9

Reference yield:

2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)acetic acid (1227484-15-2) → (S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide (1337973-23-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 1.25 h / -78 - 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.67 h / -78 °C / Inert atmosphere

2.2: 2.25 h / -78 - 20 °C / Inert atmosphere

2.3: Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.2 h / -78 °C / Inert atmosphere

3.2: 6 h / -78 - 20 °C / Inert atmosphere

4.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 4 h / 0 - 20 °C / Inert atmosphere

4.2: pH 2 - 3 / Inert atmosphere

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 10 h / 20 °C / Inert atmosphere

With n-butyllithium; lithium hydroxide monohydrate; dihydrogen peroxide; sodium hexamethyldisilazane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1007/s12272-011-0805-9

Reference yield:

C23H38O7Si → (S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)-N-methoxy-N-methylpropanamide (1337973-23-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.67 h / -78 °C / Inert atmosphere

1.2: 2.25 h / -78 - 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.2 h / -78 °C / Inert atmosphere

2.2: 6 h / -78 - 20 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 4 h / 0 - 20 °C / Inert atmosphere

3.2: pH 2 - 3 / Inert atmosphere

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 10 h / 20 °C / Inert atmosphere

With n-butyllithium; lithium hydroxide monohydrate; dihydrogen peroxide; sodium hexamethyldisilazane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1007/s12272-011-0805-9

upstream raw materials:

2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)acetic acid

(5-bromo-2-methoxy-4-(methoxymethoxy)benzyloxy)(tert-butyl)dimethylsilane

(S)-4-benzyl-3-(2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)acetyl)oxazolidin-2-one

(S)-4-benzyl-3-((S)-2-(5-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-2-(methoxymethoxy)phenyl)propanoyl)oxazolidin-2-one

Downstream raw materials:

(R)-tert-butyl(2-methoxy-4-(methoxymethoxy)-5-(3-methylbut-3-en-2-yl)benzyloxy)dimethylsilane

(R)-2-methoxy-4-(methoxymethoxy)-5-(3-methylbut-3-en-2-yl)phenylmethanol

(R)-2-methoxy-4-(methoxymethoxy)-5-(3-methylbut-3-en-2-yl)benzaldehyde

(E)-3-(2-methoxy-4-(methoxymethoxy)-5-((R)-3-methylbut-3-en-2-yl)phenyl)-1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)prop-2-en-1-one

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