methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(S_S)-3-(p-tolylsulfinyl)-2-furyl]propanoate

Base Information

• Chemical Name: methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(S_S)-3-(p-tolylsulfinyl)-2-furyl]propanoate
• CAS No.: 290836-59-8
• Molecular Formula: C₂₈H₃₇NO₆SSi
• Molecular Weight: 543.756

Synonyms:methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(S_S)-3-(p-tolylsulfinyl)-2-furyl]propanoate

Chemical Property of methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(S_S)-3-(p-tolylsulfinyl)-2-furyl]propanoate

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Technology Process of methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(S_S)-3-(p-tolylsulfinyl)-2-furyl]propanoate

There total 4 articles about methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(S_S)-3-(p-tolylsulfinyl)-2-furyl]propanoate 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: 67.0%

[(1,1-dimethylethyl)(dimethyl)silyloxy]acetic acid methyl ester (146351-72-6) + (SS)-(N-p-methoxyphenyl)-3-(p-tolylsulfinyl)-2-furaldimine (290836-53-2) → methyl (3S,4R)-3-(tert-butyldimethylsilyloxy)-1-(N-p-methoxyphenyl)-4-[(SS)-3-(p-tolylsulfinyl)-2-furyl]-2-azetidinone + methyl (3R,4R)-3-(tert-butyldimethylsilyloxy)-1-(N-p-methoxyphenyl)-4-[(SS)-3-(p-tolylsulfinyl)-2-furyl]-2-azetidinone + methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(SS)-3-(p-tolylsulfinyl)-2-furyl]propanoate (290836-59-8) + methyl (2R,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(SS)-3-(p-tolylsulfinyl)-2-furyl]propanoate (459797-67-2)

Guidance literature:

[(1,1-dimethylethyl)(dimethyl)silyloxy]acetic acid methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(S_S)-(N-p-methoxyphenyl)-3-(p-tolylsulfinyl)-2-furaldimine; In tetrahydrofuran; hexane; at -78 - -30 ℃; for 1h; Further byproducts given;

DOI:10.1248/cpb.50.615

Reference yield:

4-methoxy-aniline (104-94-9) → methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(SS)-3-(p-tolylsulfinyl)-2-furyl]propanoate (290836-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 77 percent / MgSO₄ / benzene / 20 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 67 percent / tetrahydrofuran; hexane / 1 h / -78 - -30 °C

With magnesium sulfate; lithium diisopropyl amide; In tetrahydrofuran; hexane; benzene;

DOI:10.1248/cpb.50.615

Reference yield:

3-((S)-Toluene-4-sulfinyl)-furan-2-carbaldehyde (159812-85-8) → methyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-(N-p-methoxyphenylamino)-3-[(SS)-3-(p-tolylsulfinyl)-2-furyl]propanoate (290836-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 77 percent / MgSO₄ / benzene / 20 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 67 percent / tetrahydrofuran; hexane / 1 h / -78 - -30 °C

With magnesium sulfate; lithium diisopropyl amide; In tetrahydrofuran; hexane; benzene;

DOI:10.1248/cpb.50.615

upstream raw materials:

(S_S)-(N-p-methoxyphenyl)-3-(p-tolylsulfinyl)-2-furaldimine

[(1,1-dimethylethyl)(dimethyl)silyloxy]acetic acid methyl ester

4-methoxy-aniline

3-((S)-Toluene-4-sulfinyl)-furan-2-carbaldehyde

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