N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide
• CAS No.: 209266-22-8
• Molecular Formula: C₁₆H₂₇NO₄SSi
• Molecular Weight: 357.546
• Mol file: 209266-22-8.mol

Synonyms:N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide

Chemical Property of N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide

There total 5 articles about N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide 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: 90.0%

(R)-N-(1-(tert-butyldimethylsilyloxy)-3-hydroxypropan-2-yl)-4-methylbenzenesulfonamide (188816-48-0) → N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide (209266-22-8)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; sodium bromide; In water; ethyl acetate; toluene; at 0 ℃;

DOI:10.1016/S0040-4020(98)00299-3

Reference yield:

methyl (S)-3-tret-butyldimethylsilyloxy-2-(4-methylphenylsulfamido)propanoate (209266-09-1) → N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide (209266-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1: LiBH₄ / tetrahydrofuran; ethanol / 20 h

2: 90 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy radical, NaBr, NaOCl, NaHCO₃ / toluene; ethyl acetate; H₂O / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium borohydride; sodium hydrogencarbonate; sodium bromide; In tetrahydrofuran; ethanol; water; ethyl acetate; toluene;

DOI:10.1016/S0040-4020(98)00299-3

Reference yield:

methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate (17136-46-8) → N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide (209266-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / CH₂Cl₂; dimethylformamide / 3 h / Ambient temperature

2: LiBH₄ / tetrahydrofuran; ethanol / 20 h

3: 90 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy radical, NaBr, NaOCl, NaHCO₃ / toluene; ethyl acetate; H₂O / 0 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium borohydride; sodium hydrogencarbonate; sodium bromide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(98)00299-3

upstream raw materials:

(R)-N-(1-(tert-butyldimethylsilyloxy)-3-hydroxypropan-2-yl)-4-methylbenzenesulfonamide

methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate

p-toluenesulfonyl chloride

methyl (S)-3-tret-butyldimethylsilyloxy-2-(4-methylphenylsulfamido)propanoate

Downstream raw materials:

(2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol

(2S,3R,4R,5R)-2,5-bis(hydroxymethyl)-1-tosylpyrrolidine-3,4-diol

(2S,3R,4R,5R)-2-(hydroxymethyl)-4-[dimethyl(phenyl)silyl]-5-{[dimethyl(phenyl)silyl]methyl}-1-tosylpyrrolidin-3-ol