<3aS-<3aα,4α(1E,3R^*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate

Base Information

• Chemical Name: <3aS-<3aα,4α(1E,3R^*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate
• CAS No.: 110972-05-9
• Molecular Formula: C₄₂H₇₄O₄Si₃
• Molecular Weight: 727.304

Synonyms:<3aS-<3aα,4α(1E,3R^*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate

Chemical Property of <3aS-<3aα,4α(1E,3R^*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate

Chemical Property:

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Technology Process of <3aS-<3aα,4α(1E,3R^*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate

There total 7 articles about <3aS-<3aα,4α(1E,3R^*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate 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: 86.0%

(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)(((methylthio)(thiocarbonyl))oxy)methyl>prost-13-en-5-yn-1-oate (115729-41-4) → <3aS-<3aα,4α(1E,3R*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate (110972-05-9)

Guidance literature:

With di-tert-butyl peroxide; tri-n-butyl-tin hydride; In benzene; at 65 ℃; for 4h;

DOI:10.1021/jo00234a014

Reference yield: 75.0%

(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)((m-(trifluoromethyl)benzoyl)oxy)methyl>prost-13-en-5-yn-1-oate (120787-33-9) → <3aS-<3aα,4α(1E,3R*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate (110972-05-9)

Guidance literature:

With magnesium(II) perchlorate; N-methylcarbazole; In tetrahydrofuran; water; at 18 ℃; for 16h; Irradiation;

DOI:10.1021/jo00234a014

Reference yield:

5,6-Didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGE2 methyl ester (59895-16-8) → <3aS-<3aα,4α(1E,3R*),5β,6aα>>-methyl 5-oxy>-4-<3-<<(1,1-dimethylathyl)dimethylsilyl>oxy>-1-octenyl>-1-(dimethylphenylsilyl)-2(1H)-pentalenylidene>pentanoate (110972-05-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / Zn, TiCl₄ / CH₂Cl₂ / 1 h / 0 °C

2: 1.) methyl acetate, 9-borabicyclo<3.3.1>nonane, 2.) NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 2.5 h, 2.) THF, 0 deg C, 30 min

3: 85 percent / pyridinium dichromate / CH₂Cl₂ / 11 h / 20 °C

4: 85 percent / tetrahydrofuran / 0.5 h / -78 °C

5: 90 percent / 4-(dimethylamino)pyridine / acetonitrile / 15 h / 18 °C

6: 75 percent / Mg(ClO₄)2, N-methylcarbazole / tetrahydrofuran; H₂O / 16 h / 18 °C / Irradiation

With dmap; sodium hydroxide; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; magnesium(II) perchlorate; N-methylcarbazole; acetic acid methyl ester; dihydrogen peroxide; titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1021/jo00234a014

upstream raw materials:

(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)(((methylthio)(thiocarbonyl))oxy)methyl>prost-13-en-5-yn-1-oate

(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)((m-(trifluoromethyl)benzoyl)oxy)methyl>prost-13-en-5-yn-1-oate

5,6-Didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGE₂ methyl ester

(11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-methyleneprost-13-en-5-yn-1-oate

Downstream raw materials:

isocarbacyclin

<3aS-<3aα,4α(1E,3R^*),5β,6aα>>-methyl 5-pentanoate

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