(2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester

Base Information

Chemical Name:(2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester
CAS No.:749927-03-5
Molecular Formula:C₁₉H₂₇NO₄
Molecular Weight:333.428
Hs Code.:

Synonyms:(2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester

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Chemical Property of (2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester

Chemical Property:

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Technology Process of (2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester

There total 11 articles about (2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl 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:

: 104-53-0
3-phenyl-propionaldehyde

: 749927-03-5
(2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / NaH / tetrahydrofuran / 1 h / 0 °C

2: (+)-DIP-Cl / tetrahydrofuran / 2 h / Heating

3: EDCI; DMAP / CH₂Cl₂ / 2 h / 0 °C

4: 86 percent / LDA / ZnCl₂ / tetrahydrofuran / -78 - 20 °C

5: 68 percent / HBF₄ / dioxane / 24 h / 65 °C

6: Na₂CO₃ / dioxane; H₂O / 20 °C

7: diethyl ether

With dmap; tetrafluoroboric acid; sodium hydride; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; B-chlorodiisopinocampheylborane; lithium diisopropyl amide; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; 1: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2004.05.157

Reference yield:

: 75553-23-0
(E)-5-phenyl-2-penten-1-ol

: 749927-03-5
(2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: imidazole / CH₂Cl₂ / 1 h / -78 - 20 °C

2: 80 percent / sec-BuLi; TMEDA / tetrahydrofuran / 1 h / -78 - 20 °C

3: 100 percent / H₂SO₄; CrO₃ / acetone

4: (+)-DIP-Cl / tetrahydrofuran / 2 h / Heating

5: EDCI; DMAP / CH₂Cl₂ / 2 h / 0 °C

6: 86 percent / LDA / ZnCl₂ / tetrahydrofuran / -78 - 20 °C

7: 68 percent / HBF₄ / dioxane / 24 h / 65 °C

8: Na₂CO₃ / dioxane; H₂O / 20 °C

9: diethyl ether

With 1H-imidazole; chromium(VI) oxide; dmap; tetrafluoroboric acid; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; sec.-butyllithium; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; B-chlorodiisopinocampheylborane; lithium diisopropyl amide; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetone; 2: reverse-Brook rearrangement / 3: Jones oxidation;
DOI:10.1016/j.tetlet.2004.05.157

Reference yield:

: 26429-97-0
methyl (2E)-5-phenyl-2-pentenoate

: 749927-03-5
(2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: DIBAL / CH₂Cl₂ / 1 h / -78 - 20 °C

2: imidazole / CH₂Cl₂ / 1 h / -78 - 20 °C

3: 80 percent / sec-BuLi; TMEDA / tetrahydrofuran / 1 h / -78 - 20 °C

4: 100 percent / H₂SO₄; CrO₃ / acetone

5: (+)-DIP-Cl / tetrahydrofuran / 2 h / Heating

6: EDCI; DMAP / CH₂Cl₂ / 2 h / 0 °C

7: 86 percent / LDA / ZnCl₂ / tetrahydrofuran / -78 - 20 °C

8: 68 percent / HBF₄ / dioxane / 24 h / 65 °C

9: Na₂CO₃ / dioxane; H₂O / 20 °C

10: diethyl ether

With 1H-imidazole; chromium(VI) oxide; dmap; tetrafluoroboric acid; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; sec.-butyllithium; diisobutylaluminium hydride; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; B-chlorodiisopinocampheylborane; lithium diisopropyl amide; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetone; 3: reverse-Brook rearrangement / 4: Jones oxidation;
DOI:10.1016/j.tetlet.2004.05.157