(S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester
CAS No.:360558-66-3
Molecular Formula:C₄₁H₅₁FN₄O₆
Molecular Weight:714.878
Hs Code.:

(S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

Synonyms:(S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

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Chemical Property of (S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

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Technology Process of (S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

There total 21 articles about (S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-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: 78.0%

: 150407-68-4
(S)-2-tert-butylcarboxamide-4-benzyloxycarbonylpiperazine

: 360558-48-1
(2S,3R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-3-(S)-oxiranyl-propan-1-one

: 360558-66-3
(S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

Guidance literature:: In isopropyl alcohol; at 80 ℃; for 13h;
DOI:10.1021/ja010113y

Reference yield:

: (R)-2-Fluoro-3-nitromethyl-4-phenyl-butyric acid

: 360558-66-3
(S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: (COCl)2; DMF / CH₂Cl₂ / 0 - 23 °C

2.1: 3.41 g / tetrahydrofuran; hexane / 2 h / 0 °C

3.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C

4.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C

5.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C

6.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C

6.2: sodium tetraborate; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

6.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH₂Cl₂

7.1: 88 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 23 °C

8.1: 89 percent / methanesulfonic acid / ethyl acetate / 3 h / 23 °C

9.1: 85 percent / t-BuOK / tetrahydrofuran / 0.25 h / 0 °C

10.1: 78 percent / propan-2-ol / 13 h / 80 °C

With lithium borohydride; oxalyl dichloride; methanesulfonic acid; potassium tert-butylate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; isopropyl alcohol; tert-butyl alcohol;
DOI:10.1021/ja010113y

Reference yield:

: (R)-2-Fluoro-3-nitromethyl-4-phenyl-butyryl chloride

: 360558-66-3
(S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 3.41 g / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C

3.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C

4.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C

5.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C

5.2: sodium tetraborate; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

5.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH₂Cl₂

6.1: 88 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 23 °C

7.1: 89 percent / methanesulfonic acid / ethyl acetate / 3 h / 23 °C

8.1: 85 percent / t-BuOK / tetrahydrofuran / 0.25 h / 0 °C

9.1: 78 percent / propan-2-ol / 13 h / 80 °C

With lithium borohydride; methanesulfonic acid; potassium tert-butylate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; methanol; hexane; ethyl acetate; isopropyl alcohol; tert-butyl alcohol;
DOI:10.1021/ja010113y