(Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol

Base Information

Chemical Name:(Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol
CAS No.:851889-77-5
Molecular Formula:C₃₆H₆₂O₆Si₂
Molecular Weight:647.056
Hs Code.:

(Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol

Synonyms:(Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol

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Chemical Property of (Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol

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Technology Process of (Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol

There total 18 articles about (Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol 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: 80.0%

: 851889-75-3
(2S,3R,4R,5S,7S,10S,11R,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-7-isobutyrate-1,3-[(R)-4-methoxybenzylidenedioxy]-5-hydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadec-13-en-8-yn

: 851889-77-5
(Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol

: 851889-76-4
(2S,3R,4R,5S,7S,10S,11R,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-1,7-dihydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadec-13-en-8-yn

Guidance literature:: (2S,3R,4R,5S,7S,10S,11R,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-7-isobutyrate-1,3-[(R)-4-methoxybenzylidenedioxy]-5-hydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadec-13-en-8-yn; With potassium hydroxide; In methanol; at 20 ℃;

With silica gel; In methanol; hexane;
DOI:10.1021/ja043168j

Reference yield:

: 851889-68-4
(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

: 851889-77-5
(Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone; pyridine / methanol / -78 °C

1.2: 95 percent / dimethyl sulfide / methanol / -78 - 0 °C

2.1: diisopropylethyl amine / CH₂Cl₂ / 0.08 h / -78 °C

2.2: Bu₂BOTf / CH₂Cl₂ / 0.75 h / -78 °C

2.3: 76 percent / CH₂Cl₂ / 1 h / -78 °C

3.1: 95 percent / SmI₂ / tetrahydrofuran / 4 h / -10 °C

4.1: KOH / methanol / 20 °C

4.2: 20 percent / silica gel / methanol; hexane

With pyridine; potassium hydroxide; samarium diiodide; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 3.1: Evans-Tischenko reduction;
DOI:10.1021/ja043168j

Reference yield:

: 851889-73-1
(2S,3R,4R,7S,10S,11R,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-1,3-[(R)-4-methoxybenzylidenedioxy]-7-hydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadec-13-en-8-yn-5-one

: 851889-77-5
(Z)-(2S,3S,5S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-12-trimethylsilanyl-tridec-11-en-6-yne-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 95 percent / SmI₂ / tetrahydrofuran / 4 h / -10 °C

2.1: KOH / methanol / 20 °C

2.2: 20 percent / silica gel / methanol; hexane

With potassium hydroxide; samarium diiodide; In tetrahydrofuran; methanol; 1.1: Evans-Tischenko reduction;
DOI:10.1021/ja043168j