2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester
• CAS No.: 890139-92-1
• Molecular Formula: C₄₄H₅₉N₇O₉Si
• Molecular Weight: 858.079
• Mol file: 890139-92-1.mol

Synonyms:2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester

Chemical Property of 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester

There total 8 articles about 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester 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:

(R)-5-Triisopropylsilanyloxymethyl-pyrrolidin-2-one → 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester (890139-92-1)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N; TMSCl / CH₂Cl₂ / 1.5 h / 20 °C

2: DMAP; diisopropylcarbodiimide / CH₂Cl₂ / 12 h

3: MsN₃; Et₃N / acetonitrile

4: Rh₂Oct₄ / benzene / 1.5 h / 95 °C

5: 840 mg / benzene / 12 h / 20 °C

6: N-methylmorpholine; Pd(PPh₃)4 / tetrahydrofuran / 0.5 h

7: 143 mg / N,N-diisopropylethylamine; PyBOP / CH₂Cl₂; dimethylformamide / 12 h / 20 °C

With 4-methyl-morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; Methanesulfonyl azide; diisopropyl-carbodiimide; rhodium (II) octanoate dimer; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ol0604724

Reference yield:

3-Oxo-3-((R)-2-oxo-5-triisopropylsilanyloxymethyl-pyrrolidin-1-yl)-propionic acid → 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester (890139-92-1)

Guidance literature:

Multi-step reaction with 6 steps

1: DMAP; diisopropylcarbodiimide / CH₂Cl₂ / 12 h

2: MsN₃; Et₃N / acetonitrile

3: Rh₂Oct₄ / benzene / 1.5 h / 95 °C

4: 840 mg / benzene / 12 h / 20 °C

5: N-methylmorpholine; Pd(PPh₃)4 / tetrahydrofuran / 0.5 h

6: 143 mg / N,N-diisopropylethylamine; PyBOP / CH₂Cl₂; dimethylformamide / 12 h / 20 °C

With 4-methyl-morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; Methanesulfonyl azide; diisopropyl-carbodiimide; rhodium (II) octanoate dimer; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ol0604724

Reference yield:

(R)-allyl 3-oxo-3-(2-oxo-5-((triisopropylsilyloxy)methyl)pyrrolidin-1-yl)propanoate (890140-48-4) → 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(R)-3-[3-((S)-2-phenyl-1-prop-2-ynylcarbamoyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester (890139-92-1)

Guidance literature:

Multi-step reaction with 5 steps

1: MsN₃; Et₃N / acetonitrile

2: Rh₂Oct₄ / benzene / 1.5 h / 95 °C

3: 840 mg / benzene / 12 h / 20 °C

4: N-methylmorpholine; Pd(PPh₃)4 / tetrahydrofuran / 0.5 h

5: 143 mg / N,N-diisopropylethylamine; PyBOP / CH₂Cl₂; dimethylformamide / 12 h / 20 °C

With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; Methanesulfonyl azide; rhodium (II) octanoate dimer; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ol0604724

upstream raw materials:

(S)-1-azido-3-phenylpropan-2-amine

(S)-2-amino-3-phenyl-N-(prop-2-ynyl)propanamide

(R)-allyl 3-oxo-3-(2-oxo-5-((triisopropylsilyloxy)methyl)pyrrolidin-1-yl)propanoate

2-Diazo-3-oxo-3-((R)-2-oxo-5-triisopropylsilanyloxymethyl-pyrrolidin-1-yl)-propionic acid allyl ester