(3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide

Base Information

• Chemical Name: (3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide
• CAS No.: 478491-15-5
• Molecular Formula: C₂₂H₃₁NO₄Si
• Molecular Weight: 401.578
• Mol file: 478491-15-5.mol

Synonyms:(3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide

Chemical Property of (3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide

There total 3 articles about (3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide 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: 94.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (S)-4-(((tert-butyldiphenylsilyl)oxy)methyl)oxetan-2-one (478491-03-1) → (3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide (478491-15-5)

Guidance literature:

N,O-dimethylhydroxylamine*hydrochloride; With dimethylaluminum chloride; In hexane; dichloromethane; at 20 ℃; for 1h;

(S)-4-(((tert-butyldiphenylsilyl)oxy)methyl)oxetan-2-one; In hexane; dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(02)00722-6

Reference yield: 69.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate (124655-05-6) → (3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide (478491-15-5)

Guidance literature:

With trimethylaluminum; In tetrahydrofuran; at 45 ℃; for 15h;

DOI:10.3987/COM-97-S(N)7

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide (478491-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

2: 69 percent / trimethylaluminum / tetrahydrofuran / 15 h / 45 °C

With 1H-imidazole; trimethylaluminum; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.3987/COM-97-S(N)7

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

(S)-4-(((tert-butyldiphenylsilyl)oxy)methyl)oxetan-2-one

tert-butylchlorodiphenylsilane

Downstream raw materials:

(S)-8-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyoct-5-yn-4-one

(S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyl-2H-pyran-4(3H)-one

(2S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyldihydro-2H-pyran-4(3H)-one

(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one