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

Base Information

Chemical Name:(2S,3S)-2-(2-hydroxyethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide
CAS No.:1617519-61-5
Molecular Formula:C₂₇H₂₈N₂O₄
Molecular Weight:444.53
Hs Code.:

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

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

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Technology Process of (2S,3S)-2-(2-hydroxyethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide

There total 5 articles about (2S,3S)-2-(2-hydroxyethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide 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: 91.0%

: 1617519-65-9
(2S,3S)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tet.2014.05.054

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; 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

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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: |Wolff Rearrangement / 3.2: |Wolff Rearrangement;
DOI:10.1016/j.tet.2014.05.054