(S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

Base Information

Chemical Name:(S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one
CAS No.:180250-61-7
Molecular Formula:C₂₈H₂₆N₄O₄
Molecular Weight:482.539
Hs Code.:

Synonyms:(S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

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Chemical Property of (S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

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Technology Process of (S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

There total 7 articles about (S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one 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: 84.0%

: 180250-60-6
(S)-4-Benzyl-3-[(R)-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-oxazolidin-2-one

: 180250-61-7
(S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

Guidance literature:: With 2,4,6-Triisopropylbenzenesulfonyl azide; potassium hexamethylsilazane; acetic acid; In tetrahydrofuran; 1.) -78 deg C, 0.5 h; 2.) 2 min; 3.) rt;
DOI:10.1016/0040-4039(96)00775-7

Reference yield:

: 7400-08-0,50940-26-6
p-Coumaric Acid

: 180250-61-7
(S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / Cs₂CO₃ / dimethylformamide

2: 92 percent / DIBAL, 2.5 eq. / toluene / 0 °C

3: 90 percent / (CH₃)3CCO₂H / o-xylene / 3 h / 140 °C

4: 90 percent / 3 N NaOH/CH₃OH / tetrahydrofuran / 48 h / Ambient temperature

5: (CH₃)3CCOCl, Et₃N / tetrahydrofuran / -78 - 20 °C

6: 84 percent / 1.) (TMS)2NK; 2.) 2,4,6-triisopropylbenzenesulfonyl azide; 3.) HOAc / tetrahydrofuran / 1.) -78 deg C, 0.5 h; 2.) 2 min; 3.) rt

With methanol; sodium hydroxide; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; caesium carbonate; acetic acid; triethylamine; Trimethylacetic acid; In tetrahydrofuran; o-xylene; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0040-4039(96)00775-7

Reference yield:

: 6272-45-3,227105-11-5
(E)-4-benzyloxycinnamic acid

: 180250-61-7
(S)-3-[(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / DIBAL, 2.5 eq. / toluene / 0 °C

2: 90 percent / (CH₃)3CCO₂H / o-xylene / 3 h / 140 °C

3: 90 percent / 3 N NaOH/CH₃OH / tetrahydrofuran / 48 h / Ambient temperature

4: (CH₃)3CCOCl, Et₃N / tetrahydrofuran / -78 - 20 °C

5: 84 percent / 1.) (TMS)2NK; 2.) 2,4,6-triisopropylbenzenesulfonyl azide; 3.) HOAc / tetrahydrofuran / 1.) -78 deg C, 0.5 h; 2.) 2 min; 3.) rt

With methanol; sodium hydroxide; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; acetic acid; triethylamine; Trimethylacetic acid; In tetrahydrofuran; o-xylene; toluene;
DOI:10.1016/0040-4039(96)00775-7