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
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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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%

: 1617519-61-5
(2S,3S)-2-(2-hydroxyethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide

: 1617519-66-0
2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid

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:

: 83427-81-0
(S)-N-tritylhomoserine lactone

: 1617519-66-0
2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid

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:

: 1617519-62-6
2-((3S)-2-hydroxy-3-(tritylamino)tetrahydrofuran-2-yl)-N-methoxy-N-methylacetamide

: 1617519-66-0
2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid

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