(2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester

Base Information

Chemical Name:(2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester
CAS No.:563539-39-9
Molecular Formula:C₁₆H₂₀N₂O₂
Molecular Weight:272.347
Hs Code.:

Synonyms:(2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester

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Chemical Property of (2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester

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Technology Process of (2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester

There total 7 articles about (2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl 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: 47.0%

: 563539-36-6
(2E,4S)-4-(benzyl-cyanomethyl-amino)-pent-2-enoic acid ethyl ester

: 563539-38-8
(2S,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester

: 563539-39-9
(2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -10 ℃; for 2h;
DOI:10.1039/b509514j

Reference yield:

: 65943-49-9,86941-35-7,86941-38-0,40916-81-2
(S)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-propan-1-ol

: 563539-39-9
(2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: sodium borohydride / ethanol / 2 h / 20 °C

2: 68 percent / K₂CO₃ / acetonitrile / 2.5 h / Heating

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

4: CH₂Cl₂ / -78 - 20 °C

5: 27 percent / LiHMDS / tetrahydrofuran / 2 h / -78 - -10 °C

With sodium tetrahydroborate; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; 3: Swern oxidation / 4: Wittig olefination;
DOI:10.1039/b509514j

Reference yield:

: 6940-80-3,6940-81-4
(S)-N-benzylalaninol

: 563539-39-9
(2R,3S,4S)-(1-benzyl-2-cyano-4-methyl-azetidin-3-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 68 percent / K₂CO₃ / acetonitrile / 2.5 h / Heating

2: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

3: CH₂Cl₂ / -78 - 20 °C

4: 27 percent / LiHMDS / tetrahydrofuran / 2 h / -78 - -10 °C

With oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetonitrile; 2: Swern oxidation / 3: Wittig olefination;
DOI:10.1039/b509514j