4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester
• CAS No.: 1027381-62-9
• Molecular Formula: C₃₆H₄₁N₃O₄Si
• Molecular Weight: 607.825

Synonyms:4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester

Chemical Property of 4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester

There total 8 articles about 4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl 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:

hydrogen cyanide (74-90-8) + 1-amino-2-propene (107-11-9,30551-89-4) + 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(2-oxo-ethyl)-3-isoxazolecarboxylic acid ethyl ester (691407-06-4) → 4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester (1027381-62-9)

Guidance literature:

1-amino-2-propene; 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(2-oxo-ethyl)-3-isoxazolecarboxylic acid ethyl ester; In toluene; for 0.0166667h;

hydrogen cyanide; With (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine; In toluene; at -78 - 20 ℃; for 49h;

DOI:10.1021/ol049619m

Reference yield:

5-[(2,2-ketophenyl)ethyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl) 3-isoxazolecarboxylic acid ethyl ester (646066-64-0) → 4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester (1027381-62-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (R)-2-methyl-CBS-oxazaborolidine; dimethyl sulfide borane complex / CH₂Cl₂; toluene; tetrahydrofuran / 24 h / -45 °C

2.1: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

3.1: p-toluenesulfonic acid monohydrate / acetone

4.1: BF₃*OEt₂ / 0.17 h / cooling

4.2: lead(IV) acetate / benzene

5.1: borane dimethyl sulfide complex / tetrahydrofuran / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

7.1: toluene / 0.02 h

7.2: L,R,R-Jacobsen peptide / toluene / 49 h / -78 - 20 °C

With 1H-imidazole; dmap; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dimethyl sulfide borane; Dess-Martin periodane; toluene-4-sulfonic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; acetone; toluene; 6.1: Dess-Martin oxidation / 7.2: Jacobsen-Strecker reaction;

DOI:10.1021/ol049619m

Reference yield:

3-isoxazolecarboxylic acid 5-[(2,2-hydroxyphenyl)ethyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester (386707-48-8) → 4-((S)-2-Allylamino-2-cyano-ethyl)-5-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-ethyl]-isoxazole-3-carboxylic acid ethyl ester (1027381-62-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

2.1: (R)-2-methyl-CBS-oxazaborolidine; dimethyl sulfide borane complex / CH₂Cl₂; toluene; tetrahydrofuran / 24 h / -45 °C

3.1: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

4.1: p-toluenesulfonic acid monohydrate / acetone

5.1: BF₃*OEt₂ / 0.17 h / cooling

5.2: lead(IV) acetate / benzene

6.1: borane dimethyl sulfide complex / tetrahydrofuran / 20 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

8.1: toluene / 0.02 h

8.2: L,R,R-Jacobsen peptide / toluene / 49 h / -78 - 20 °C

With 1H-imidazole; dmap; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dimethyl sulfide borane; Dess-Martin periodane; toluene-4-sulfonic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; acetone; toluene; 1.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 8.2: Jacobsen-Strecker reaction;

DOI:10.1021/ol049619m

upstream raw materials:

hydrogen cyanide

1-amino-2-propene

5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(2-oxo-ethyl)-3-isoxazolecarboxylic acid ethyl ester

5-[(2,2-ketophenyl)ethyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl) 3-isoxazolecarboxylic acid ethyl ester

Downstream raw materials:

(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(N-allyl-2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

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