5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester

Base Information

Chemical Name:5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester
CAS No.:691407-02-0
Molecular Formula:C₃₂H₃₅NO₅Si
Molecular Weight:541.719
Hs Code.:

Synonyms:5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester

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Chemical Property of 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester

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Technology Process of 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester

There total 4 articles about 5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-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:

: 691407-00-8
(S)-5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-3-isoxazolecarboxylic acid ethyl ester

: 691407-02-0
5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester

Guidance literature:: With toluene-4-sulfonic acid; In acetone;
DOI:10.1021/ol049619m

Reference yield:

: 646066-64-0
5-[(2,2-ketophenyl)ethyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl) 3-isoxazolecarboxylic acid ethyl ester

: 691407-02-0
5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: p-toluenesulfonic acid monohydrate / acetone

With 1H-imidazole; dmap; 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:

: 386707-48-8
3-isoxazolecarboxylic acid 5-[(2,2-hydroxyphenyl)ethyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester

: 691407-02-0
5-(2-phenyl-2-(t-butyldiphenylsilyloxy)-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

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

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

4: p-toluenesulfonic acid monohydrate / acetone

With 1H-imidazole; dmap; 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: Dess-Martin oxidation;
DOI:10.1021/ol049619m