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

Base Information

• Chemical Name: 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
• CAS No.: 735317-43-8
• Molecular Formula: C₃₉H₅₁NO₆Si
• Molecular Weight: 657.923

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 11 articles about 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 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: 65.0%

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 (735317-39-2) → 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 (735317-43-8)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; water; for 0.0833333h;

DOI:10.1021/ol0490633

Reference yield:

(S)-(-)-Z-3-penten-2-ol (926-58-9,1569-50-2,3899-34-1,24652-50-4,35666-69-4,42569-15-3,42569-16-4,60102-79-6,60102-80-9,79646-46-1,95782-14-2,31001-81-7) → 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 (735317-43-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: t-BuOCl / CH₂Cl₂ / -78 °C

1.2: EtMgBr; i-PrOH / CH₂Cl₂ / 0 - 23 °C

2.1: 98 percent / imidazole / dimethylformamide / 22 h

3.1: 95 percent / AcOH; H₂O / tetrahydrofuran / 30 h / 23 °C

4.1: 99 percent / PPh₃; DEAD / tetrahydrofuran / 1.5 h

5.1: 92 percent / Mo₇O₂₄(NH₄)6*4H₂O; aq. H₂O₂ / ethanol / 18 h / 50 °C

6.1: 31 percent / KHMDS / tetrahydrofuran / 1.5 h / -78 - -25 °C

7.1: 65 percent / SmI₂ / tetrahydrofuran; H₂O / 0.08 h

With 1H-imidazole; samarium diiodide; ammonium molybdate tetrahydrate; tert-butylhypochlorite; water; dihydrogen peroxide; potassium hexamethylsilazane; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol0490633

Reference yield:

(S)-1-{(4R,5S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-methyl-4,5-dihydro-isoxazol-5-yl}-ethanol (356068-55-8) → 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 (735317-43-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / imidazole / dimethylformamide / 22 h

2: 95 percent / AcOH; H₂O / tetrahydrofuran / 30 h / 23 °C

3: 99 percent / PPh₃; DEAD / tetrahydrofuran / 1.5 h

4: 92 percent / Mo₇O₂₄(NH₄)6*4H₂O; aq. H₂O₂ / ethanol / 18 h / 50 °C

5: 31 percent / KHMDS / tetrahydrofuran / 1.5 h / -78 - -25 °C

6: 65 percent / SmI₂ / tetrahydrofuran; H₂O / 0.08 h

With 1H-imidazole; samarium diiodide; ammonium molybdate tetrahydrate; water; dihydrogen peroxide; potassium hexamethylsilazane; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ol0490633

upstream raw materials:

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

(S)-(-)-Z-3-penten-2-ol

(S)-1-{(4R,5S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-methyl-4,5-dihydro-isoxazol-5-yl}-ethanol

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

Downstream raw materials:

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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