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

Base Information

Chemical Name:(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)hydroxymethyl>prost-13-en-5-yn-1-oate
CAS No.:115729-47-0
Molecular Formula:C₄₂H₇₄O₅Si₃
Molecular Weight:743.303
Hs Code.:

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

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

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

There total 3 articles about (9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)hydroxymethyl>prost-13-en-5-yn-1-oate 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%

: 110972-01-5
(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-formylprost-13-en-5-yn-1-oate

: 115729-47-0
(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)hydroxymethyl>prost-13-en-5-yn-1-oate

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1021/jo00234a014

Reference yield:

: 59895-16-8
5,6-Didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGE₂ methyl ester

: 115729-47-0
(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)hydroxymethyl>prost-13-en-5-yn-1-oate

Guidance literature:: Multi-step reaction with 4 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

With sodium hydroxide; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; acetic acid methyl ester; dihydrogen peroxide; titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00234a014

Reference yield:

: 110971-99-8
(11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-methyleneprost-13-en-5-yn-1-oate

: 115729-47-0
(9α,11α,13E,15S)-methyl 11,15-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-9-<(dimethylphenylsilyl)hydroxymethyl>prost-13-en-5-yn-1-oate

Guidance literature:: Multi-step reaction with 3 steps

1: 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

2: 85 percent / pyridinium dichromate / CH₂Cl₂ / 11 h / 20 °C

3: 85 percent / tetrahydrofuran / 0.5 h / -78 °C

With sodium hydroxide; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; acetic acid methyl ester; dihydrogen peroxide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00234a014