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

Base Information

• Chemical Name: 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic acid ethyl ester
• CAS No.: 691407-04-2
• Molecular Formula: C₃₃H₃₇NO₆Si
• Molecular Weight: 571.745

Synonyms:5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic acid ethyl ester

Chemical Property of 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic acid ethyl ester

There total 5 articles about 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic 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:

5-[(2,2-ketophenyl)ethyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl) 3-isoxazolecarboxylic acid ethyl ester (646066-64-0) → 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic acid ethyl ester (691407-04-2)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; dmap; boron trifluoride diethyl etherate; dimethyl sulfide borane; toluene-4-sulfonic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; acetone; toluene;

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) → 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic acid ethyl ester (691407-04-2)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; dmap; 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;

DOI:10.1021/ol049619m

Reference yield:

5-(2-phenyl-2-hydroxy-ethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-3-isoxazolecarboxylic acid ethyl ester (691406-98-1) → 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-methoxycarbonylmethyl-3-isoxazolecarboxylic acid ethyl ester (691407-04-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: p-toluenesulfonic acid monohydrate / acetone

3.1: BF₃*OEt₂ / 0.17 h / cooling

3.2: lead(IV) acetate / benzene

With 1H-imidazole; dmap; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In dichloromethane; acetone;

DOI:10.1021/ol049619m

upstream raw materials:

methanol

5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-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

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

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

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

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