(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester

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Chemical Name:(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester
CAS No.:157435-88-6
Molecular Formula:C₂₁H₂₀N₄O₅
Molecular Weight:408.414
Hs Code.:

Synonyms:(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester

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Chemical Property of (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester

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Technology Process of (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester

There total 12 articles about (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl 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:

: 93740-92-2
Hexanedioic acid 3-oxo-1-methyl-6-(1,1-dimethylethyl)ester

: 157435-88-6
(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / H₂ / S-Ru-BINAP / methanol; tetrahydrofuran / 20 h / 65 °C / 2585.7 Torr

2: 1.) Me₃Al / 1.) CH₂Cl₂, hexane, ice bath cooling to r.t., 1 h, 2.) CH₂Cl₂, overnight

3: 90 percent / PPh₃, CCl₄, Et₃N / acetonitrile

4: H₂ / 10percent Pd/C / methanol / 1.5 h

5: Et₃N / CH₂Cl₂ / 0.5 h

6: 67 percent / i-Pr₂NEt, TMSN₃ / acetonitrile / 48 h

7: 73 percent / Cs₂CO₃ / acetonitrile / 4 h

8: 82 percent / anisole, TFA / 0.25 h

9: 1.) Et₃N, phenyl chloroformate / 1.) THF, ice bath cooling, 5 min, 2.) 3 h

With tetrachloromethane; trimethylsilylazide; hydrogen; trimethylaluminum; caesium carbonate; methoxybenzene; triethylamine; N-ethyl-N,N-diisopropylamine; phenyl chloroformate; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; S-Ru-BINAP; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00096a031

Reference yield:

: 157435-79-5
(S)-Hexanedioic acid 3-hydroxy-1-methyl-6-(1,1-dimethylethyl)ester

: 157435-88-6
(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) Me₃Al / 1.) CH₂Cl₂, hexane, ice bath cooling to r.t., 1 h, 2.) CH₂Cl₂, overnight

2: 90 percent / PPh₃, CCl₄, Et₃N / acetonitrile

3: H₂ / 10percent Pd/C / methanol / 1.5 h

4: Et₃N / CH₂Cl₂ / 0.5 h

5: 67 percent / i-Pr₂NEt, TMSN₃ / acetonitrile / 48 h

6: 73 percent / Cs₂CO₃ / acetonitrile / 4 h

7: 82 percent / anisole, TFA / 0.25 h

8: 1.) Et₃N, phenyl chloroformate / 1.) THF, ice bath cooling, 5 min, 2.) 3 h

With tetrachloromethane; trimethylsilylazide; hydrogen; trimethylaluminum; caesium carbonate; methoxybenzene; triethylamine; N-ethyl-N,N-diisopropylamine; phenyl chloroformate; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00096a031

Reference yield:

: 157435-81-9
(S)-Hexanoic acid 4-hydroxy-6-oxo-6-<(phenylmethoxy)amino>-(1,1-dimethylethyl) ester

: 157435-88-6
(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / PPh₃, CCl₄, Et₃N / acetonitrile

2: H₂ / 10percent Pd/C / methanol / 1.5 h

3: Et₃N / CH₂Cl₂ / 0.5 h

4: 67 percent / i-Pr₂NEt, TMSN₃ / acetonitrile / 48 h

5: 73 percent / Cs₂CO₃ / acetonitrile / 4 h

6: 82 percent / anisole, TFA / 0.25 h

7: 1.) Et₃N, phenyl chloroformate / 1.) THF, ice bath cooling, 5 min, 2.) 3 h

With tetrachloromethane; trimethylsilylazide; hydrogen; caesium carbonate; methoxybenzene; triethylamine; N-ethyl-N,N-diisopropylamine; phenyl chloroformate; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00096a031