(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl ester

Base Information

Chemical Name:(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl ester
CAS No.:180250-62-8
Molecular Formula:C₂₂H₂₅N₃O₃
Molecular Weight:379.459
Hs Code.:

Synonyms:(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl ester

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Chemical Property of (2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl ester

Chemical Property:

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Technology Process of (2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl ester

There total 9 articles about (2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl 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: 78.0%

: 98946-18-0
tert-Butyl 2,2,2-trichloroacetimidate

: 180250-65-1
(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid

: 180250-62-8
(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane;
DOI:10.1016/0040-4039(96)00775-7

Reference yield:

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

: 180250-62-8
(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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

7: 72 percent / LiOH / tetrahydrofuran; H₂O

8: 78 percent / BF₃*OEt₂ / CH₂Cl₂

With methanol; lithium hydroxide; sodium hydroxide; boron trifluoride diethyl etherate; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; caesium carbonate; acetic acid; triethylamine; Trimethylacetic acid; In tetrahydrofuran; dichloromethane; o-xylene; water; 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

: 180250-62-8
(2S,3R)-2-Azido-3-(4-benzyloxy-phenyl)-pent-4-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 72 percent / LiOH / tetrahydrofuran; H₂O

7: 78 percent / BF₃*OEt₂ / CH₂Cl₂

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