6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid methyl ester

Base Information

• Chemical Name: 6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid methyl ester
• CAS No.: 919096-66-5
• Molecular Formula: C₃₇H₄₀O₄
• Molecular Weight: 548.722

Synonyms:6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid methyl ester

Chemical Property of 6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid methyl ester

There total 16 articles about 6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid methyl 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: 85.0%

3-[7-methyl-9-(2-methyl-buta-1,3-dienyl)-3-trityloxy-2,3,4,5,8,9-hexahydro-oxonin-2-yl]-acrylic acid methyl ester (919096-67-6) → 6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.02,7]pentadeca-5,10-diene-3-carboxylic acid methyl ester (919096-66-5)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; In xylene; for 1h; Heating;

DOI:10.1021/ja065782w

Reference yield:

2-(4-methoxy-benzyloxy)-7-methyl-oct-6-ene-1,3-diol (919096-71-2) → 6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.02,7]pentadeca-5,10-diene-3-carboxylic acid methyl ester (919096-66-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 92 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 93 percent / DMAP; pyridine / 6 h / 100 °C

3.1: 88 percent / DDQ; aq. phosphate buffer / CH₂Cl₂ / 1 h / 0 °C / pH 8.0

4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

4.2: 88 percent / tetrahydrofuran / 3 h / 20 °C

5.1: SeO₂ / pyridine; ethanol / 6 h / 80 °C

5.2: 924.0 mg / NaBH₄ / ethanol / 0.5 h / 0 °C

6.1: 93 percent / CCl₄; PPh₃; pyridine / 2 h / Heating

7.1: 92 percent / LiHMDS / tetrahydrofuran / 1 h / 45 °C

8.1: n-BuLi; DIBAL-H / tetrahydrofuran; hexane; toluene / 0.5 h / 0 - 20 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

9.2: tetrahydrofuran; hexane / 1 h / -78 °C

9.3: 93.6 mg / aq. oxalic acid / tetrahydrofuran; hexane; diethyl ether / 1 h / 20 °C

10.1: NaHMDS / tetrahydrofuran / -78 - 0 °C

10.2: 97 percent / tetrahydrofuran / 2 h / -78 - 20 °C

11.1: 93 percent / TBAF / tetrahydrofuran; dimethylformamide / 16 h / 20 °C

12.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

13.1: 36.9 mg / CH₂Cl₂ / 1 h / 20 °C

14.1: 85 percent / 2,6-di-t-butyl-4-methylphenol / xylene / 1 h / Heating

With pyridine; 1H-imidazole; tetrachloromethane; dmap; n-butyllithium; selenium(IV) oxide; phosphate buffer; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; xylene; 9.2: Corey olefination / 10.2: Wittig methylenation / 12.1: Dess-Martin oxidation / 13.1: Wittig reaction / 14.1: Diels-Alder reaction;

DOI:10.1021/ja065782w

Reference yield:

4-benzyl-3-[3-hydroxy-2-(4-methoxy-benzyloxy)-7-methyl-oct-6-enoyl]-oxazolidin-2-one (919096-70-1) → 6,10-dimethyl-14-trityloxy-15-oxa-tricyclo[6.6.1.02,7]pentadeca-5,10-diene-3-carboxylic acid methyl ester (919096-66-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 89 percent / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: 92 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 93 percent / DMAP; pyridine / 6 h / 100 °C

4.1: 88 percent / DDQ; aq. phosphate buffer / CH₂Cl₂ / 1 h / 0 °C / pH 8.0

5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

5.2: 88 percent / tetrahydrofuran / 3 h / 20 °C

6.1: SeO₂ / pyridine; ethanol / 6 h / 80 °C

6.2: 924.0 mg / NaBH₄ / ethanol / 0.5 h / 0 °C

7.1: 93 percent / CCl₄; PPh₃; pyridine / 2 h / Heating

8.1: 92 percent / LiHMDS / tetrahydrofuran / 1 h / 45 °C

9.1: n-BuLi; DIBAL-H / tetrahydrofuran; hexane; toluene / 0.5 h / 0 - 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

10.2: tetrahydrofuran; hexane / 1 h / -78 °C

10.3: 93.6 mg / aq. oxalic acid / tetrahydrofuran; hexane; diethyl ether / 1 h / 20 °C

11.1: NaHMDS / tetrahydrofuran / -78 - 0 °C

11.2: 97 percent / tetrahydrofuran / 2 h / -78 - 20 °C

12.1: 93 percent / TBAF / tetrahydrofuran; dimethylformamide / 16 h / 20 °C

13.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

14.1: 36.9 mg / CH₂Cl₂ / 1 h / 20 °C

15.1: 85 percent / 2,6-di-t-butyl-4-methylphenol / xylene / 1 h / Heating

With pyridine; 1H-imidazole; tetrachloromethane; dmap; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; phosphate buffer; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; xylene; 10.2: Corey olefination / 11.2: Wittig methylenation / 13.1: Dess-Martin oxidation / 14.1: Wittig reaction / 15.1: Diels-Alder reaction;

DOI:10.1021/ja065782w

upstream raw materials:

3-[7-methyl-9-(2-methyl-buta-1,3-dienyl)-3-trityloxy-2,3,4,5,8,9-hexahydro-oxonin-2-yl]-acrylic acid methyl ester

2-(4-methoxy-benzyloxy)-7-methyl-oct-6-ene-1,3-diol

4-benzyl-3-[3-hydroxy-2-(4-methoxy-benzyloxy)-7-methyl-oct-6-enoyl]-oxazolidin-2-one

1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-7-methyl-oct-6-en-3-ol

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