(2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester
CAS No.:441786-69-2
Molecular Formula:C₂₅H₂₃NO₅
Molecular Weight:417.461
Hs Code.:

Synonyms:(2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester

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Chemical Property of (2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester

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Technology Process of (2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester

There total 12 articles about (2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl 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:

: 441786-68-1
(3S,4S)-1-(4-methoxyphenyl)-3-[4-(2-propenyloxy)phenylmethyl]-4-benzyloxycarbonylazetidin-2-one

: 441786-69-2
(2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester

Guidance literature:: (3S,4S)-1-(4-methoxyphenyl)-3-[4-(2-propenyloxy)phenylmethyl]-4-benzyloxycarbonylazetidin-2-one; With triphenylphosphine; palladium diacetate; In ethanol; for 1h; Heating;

With silica gel; at 20 ℃; for 0.0833333h;
DOI:10.1016/S0968-0896(02)00017-2

Reference yield:

: 100-39-0
benzyl bromide

: 441786-69-2
(2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 0.031 g / K₂CO₃ / acetone / 2.5 h / 20 °C

2.1: PPh₃ / Pd(OAc)2 / ethanol / 1 h / Heating

2.2: wet SiO₂ / 0.08 h / 20 °C

With potassium carbonate; triphenylphosphine; palladium diacetate; In ethanol; acetone;
DOI:10.1016/S0968-0896(02)00017-2

Reference yield:

: [(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

: 441786-69-2
(2S,3S)-3-(4-Hydroxy-benzyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 65 percent / TiCl₄; Et₃N / CH₂Cl₂ / 6 h / -78 °C

2.1: 94 percent / aq. NaOH / methanol / 2 h

3.1: 85 percent / P₂O₅ / dimethylsulfoxide / 20 h / 20 °C

4.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -20 °C

4.2: 73 percent / tetrahydrofuran; hexane / 2 h / -20 °C

5.1: 98 percent / H₂ / 10 percent Pd/C / ethanol / 3 h / 20 °C

6.1: 100 percent / K₂CO₃ / acetonitrile / 60 h / 50 °C

7.1: TFA / H₂O / 0 - 20 °C

8.1: 0.033 g / NaIO₄ / ethyl acetate; H₂O / 2 h / 0 °C

9.1: CrO₃; conc. H₂SO₄ / H₂O; acetone / 0.25 h / 20 °C

10.1: 0.031 g / K₂CO₃ / acetone / 2.5 h / 20 °C

11.1: PPh₃ / Pd(OAc)2 / ethanol / 1 h / Heating

11.2: wet SiO₂ / 0.08 h / 20 °C

With chromium(VI) oxide; sodium hydroxide; sodium periodate; n-butyllithium; sulfuric acid; hydrogen; phosphorus pentoxide; titanium tetrachloride; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone; acetonitrile; 4.2: Wittig reaction;
DOI:10.1016/S0968-0896(02)00017-2