2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid

Base Information

• Chemical Name: 2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid
• CAS No.: 1617519-66-0
• Molecular Formula: C₂₇H₂₆N₂O₅
• Molecular Weight: 458.514
• Mol file: 1617519-66-0.mol

Synonyms:2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid

Chemical Property of 2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid

There total 6 articles about 2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid 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%

(2S,3S)-2-(2-hydroxyethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide (1617519-61-5) → 2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid (1617519-66-0)

Guidance literature:

With sodium periodate; rhodium(III) chloride hydrate; In tetrachloromethane; water; acetonitrile; at 20 ℃;

DOI:10.1016/j.tet.2014.05.054

Reference yield:

(S)-N-tritylhomoserine lactone (83427-81-0) → 2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid (1617519-66-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C

1.2: 0.25 h

1.3: 2 h / 0 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / 20 °C / Inert atmosphere

4.1: toluene / 4.5 h / 0 °C / Irradiation

4.2: 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

6.1: sodium periodate; rhodium(III) chloride hydrate / water; acetonitrile; tetrachloromethane / 20 °C

With 1H-imidazole; sodium periodate; n-butyllithium; rhodium(III) chloride hydrate; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; tetrachloromethane; hexane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: |Wolff Rearrangement / 4.2: |Wolff Rearrangement;

DOI:10.1016/j.tet.2014.05.054

Reference yield:

2-((3S)-2-hydroxy-3-(tritylamino)tetrahydrofuran-2-yl)-N-methoxy-N-methylacetamide (1617519-62-6) → 2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid (1617519-66-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / 20 °C / Inert atmosphere

3.1: toluene / 4.5 h / 0 °C / Irradiation

3.2: 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

5.1: sodium periodate; rhodium(III) chloride hydrate / water; acetonitrile; tetrachloromethane / 20 °C

With 1H-imidazole; sodium periodate; rhodium(III) chloride hydrate; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; tetrachloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: |Wolff Rearrangement / 3.2: |Wolff Rearrangement;

DOI:10.1016/j.tet.2014.05.054

upstream raw materials:

(S)-N-tritylhomoserine lactone

2-((3S)-2-hydroxy-3-(tritylamino)tetrahydrofuran-2-yl)-N-methoxy-N-methylacetamide

(S)-6-((tert-butyldimethylsilyl)oxy)-N-methoxy-N-methyl-3-oxo-4-(tritylamino)hexanamide

(S)-6-((tert-butyldimethylsilyl)oxy)-2-diazo-N-methoxy-N-methyl-3-oxo-4-(tritylamino)hexanamide

Downstream raw materials:

(2S,3S)-2-(2-(benzylamino)-2-oxoethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide

(1R,5S)-2-benzyl-N-methoxy-N-methyl-3,7-dioxo-6-trityl-2,6-diazabicyclo[3.2.0]heptane-1-carboxamide