(E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid

Base Information

Chemical Name:(E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid
CAS No.:340185-19-5
Molecular Formula:C₄₁H₅₈O₆Si
Molecular Weight:674.993
Hs Code.:

Synonyms:(E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid

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Chemical Property of (E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid

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Technology Process of (E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid

There total 17 articles about (E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid 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:

: (E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid

: 340185-19-5
(E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid

Guidance literature:: With pyridine; hydrogen fluoride; In acetonitrile; at 20 ℃;
DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F

Reference yield:

: 74080-51-6
<2R,3S>-3-methyl-4-penten-2-ol

: 340185-19-5
(E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / imidazole; DMAP / dimethylformamide / 20 °C

2.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

2.2: 85 percent / aq. K₃PO₄ / [PdCl₂(bis(diphenylphosphanyl)ferrocene)] / dimethylformamide / 5 h / 25 °C

3.1: 89 percent / aq. HF; pyridine / 20 °C

4.1: 96 percent / MnO₂ / CH₂Cl₂ / 20 °C

5.1: sec-BuLi / diethyl ether / 0.17 h / -78 °C

5.2: 68 percent / diethyl ether / 0.17 h

6.1: 90 percent / imidazole; DMAP / dimethylformamide / 50 °C

7.1: 9-BBN / tetrahydrofuran / 50 °C

7.2: 78 percent / aq. H₂O₂; NaOH

8.1: o-iodoxybenzoic acid; 1-hydroxy-1,2-benziodoxol-3(1H)-one-1-oxide / tetrahydrofuran; dimethylformamide / 20 °C

9.1: NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 20 °C

10.1: aq. HF; pyridine / acetonitrile / 20 °C

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; hydrogen fluoride; sec.-butyllithium; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F

Reference yield:

: 122566-52-3
(S)-(-)-3-methylhex-5-ene-1,3-diol

: 340185-19-5
(E)-(4R,12S,13R)-7-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradec-8-enoic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: 99 percent / DMAP; imidazole / dimethylformamide / 20 °C

2.1: TfOH / diethyl ether / 0 °C

3.1: TBAF*3H₂O / tetrahydrofuran / 50 °C

4.1: 90 percent / I₂; imidazole; PPh₃ / CH₂Cl₂ / 20 °C

5.1: sec-BuLi / diethyl ether / 0.17 h / -78 °C

5.2: 68 percent / diethyl ether / 0.17 h

6.1: 90 percent / imidazole; DMAP / dimethylformamide / 50 °C

7.1: 9-BBN / tetrahydrofuran / 50 °C

7.2: 78 percent / aq. H₂O₂; NaOH

8.1: o-iodoxybenzoic acid; 1-hydroxy-1,2-benziodoxol-3(1H)-one-1-oxide / tetrahydrofuran; dimethylformamide / 20 °C

9.1: NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 20 °C

10.1: aq. HF; pyridine / acetonitrile / 20 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; trifluorormethanesulfonic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; iodine; sec.-butyllithium; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F