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

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Chemical Name:(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azido-(1,1-dimethylethyl) ester
CAS No.:157435-86-4
Molecular Formula:C₁₉H₂₄N₄O₅
Molecular Weight:388.423
Hs Code.:

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

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

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

There total 11 articles about (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azido-(1,1-dimethylethyl) 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: 73.0%

: 157435-85-3
(2R,3R)-2-Azetidinepropanoic acid, 3-azido-4-oxo-2-(1,1-dimethylethyl) ester

: 5437-45-6
Benzyl bromoacetate

: 157435-86-4
(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azido-(1,1-dimethylethyl) ester

Guidance literature:: With caesium carbonate; In acetonitrile; for 4h;
DOI:10.1021/jo00096a031

Reference yield:

: 15026-17-2
succinic acid mono-tert-butyl ester

: 157435-86-4
(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azido-(1,1-dimethylethyl) ester

Guidance literature:: Multi-step reaction with 8 steps

2: 90 percent / H₂ / S-Ru-BINAP / methanol; tetrahydrofuran / 20 h / 65 °C / 2585.7 Torr

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

4: 90 percent / PPh₃, CCl₄, Et₃N / acetonitrile

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

6: Et₃N / CH₂Cl₂ / 0.5 h

7: 67 percent / i-Pr₂NEt, TMSN₃ / acetonitrile / 48 h

8: 73 percent / Cs₂CO₃ / acetonitrile / 4 h

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

Reference yield:

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

: 157435-86-4
(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azido-(1,1-dimethylethyl) ester

Guidance literature:: Multi-step reaction with 7 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

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