Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester

Base Information

• Chemical Name: Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester
• CAS No.: 735317-59-6
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293

Synonyms:Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester

Chemical Property of Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester

There total 2 articles about Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-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: 93.0%

Benzoic acid (R)-1-[(4S,5R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-4,5-dihydro-isoxazol-5-yl]-ethyl ester (735317-57-4) → Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester (735317-59-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;

DOI:10.1021/ol0490633

Reference yield:

(R)-1-[(4S,5R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-4,5-dihydro-isoxazol-5-yl]-ethanol (735317-55-2) → Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester (735317-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 23 °C

2: 93 percent / TBAF / tetrahydrofuran / 1 h

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0490633

Reference yield: 88.0%

Benzoic acid (R)-1-((4S,5R)-3-hydroxymethyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester (735317-59-6) → Benzoic acid (R)-1-((4S,5R)-3-formyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester (735317-37-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 1.83333h;

DOI:10.1021/ol0490633

upstream raw materials:

Benzoic acid (R)-1-[(4S,5R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-4,5-dihydro-isoxazol-5-yl]-ethyl ester

(R)-1-[(4S,5R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-4,5-dihydro-isoxazol-5-yl]-ethanol

Downstream raw materials:

Benzoic acid (R)-1-((4S,5R)-3-formyl-4-methyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester

Benzoic acid (R)-1-[(4S,5R)-3-((E)-(S)-3-{(4R,5S)-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methyl-4,5-dihydro-isoxazol-3-yl}-but-1-enyl)-4-methyl-4,5-dihydro-isoxazol-5-yl]-ethyl ester

Benzoic acid (1R,2R,3R,7S)-7-{(4R,5S)-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methyl-4,5-dihydro-isoxazol-3-yl}-2-hydroxy-1,3-dimethyl-4-oxo-octyl ester

Benzoic acid (R)-1-[(4R,5S,6S)-6-((S)-3-{(4R,5S)-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methyl-4,5-dihydro-isoxazol-3-yl}-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethyl ester

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