(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

Base Information

Chemical Name:(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
CAS No.:851889-75-3
Molecular Formula:C₄₀H₆₈O₇Si₂
Molecular Weight:717.147
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 16 articles about (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 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:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / p-toluenesulfonic acid / dimethylformamide / 3 h / 20 °C

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

2.2: 95 percent / dimethyl sulfide / methanol / -78 - 0 °C

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

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

3.3: 76 percent / CH₂Cl₂ / 1 h / -78 °C

4.1: 95 percent / SmI₂ / tetrahydrofuran / 4 h / -10 °C

With pyridine; samarium diiodide; toluene-4-sulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Evans-Tischenko reduction;
DOI:10.1021/ja043168j

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

Guidance literature:: Multi-step reaction with 12 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

2.1: ozone / methanol / -78 °C

2.2: dimethyl sulfide / methanol / -78 - 0 °C

3.1: 10.7 g / triphenylphosphine; 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -20 °C

4.2: 79 percent / tetrahydrofuran; hexane / 8 h / -78 - 0 °C

5.1: Cp₂Zr(H)Cl / tetrahydrofuran / 1.08 h / 20 - 55 °C

5.2: 92 percent / I₂ / tetrahydrofuran / 0.33 h / 20 °C

6.1: ZnCl₂ / tetrahydrofuran; diethyl ether / 0.25 h / 20 °C

6.2: 88 percent / Pd(PPh₃)4 / tetrahydrofuran; diethyl ether / 2 h / 20 °C

7.1: 95 percent / lithium di-tert-butylbiphenyl radical anion / tetrahydrofuran / 2.5 h / -78 °C

8.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: 5.62 g / triphenylphosphine; 2,6-ludidine / CH₂Cl₂ / 4 h / 0 °C

10.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -20 °C

10.2: 78 percent / tetrahydrofuran; hexane / 10 h / -78 - -30 °C

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

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

11.3: 76 percent / CH₂Cl₂ / 1 h / -78 °C

12.1: 95 percent / SmI₂ / tetrahydrofuran / 4 h / -10 °C

With 2,6-dimethylpyridine; Schwartz's reagent; n-butyllithium; samarium diiodide; oxalyl dichloride; lithium 4,4′-di-tert-butylbiphenylide; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 3.1: Corey-Fuchs olefination / 8.1: Swern oxidation / 9.1: Corey-Fuchs olefination / 12.1: Evans-Tischenko reduction;
DOI:10.1021/ja043168j