(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

Base Information

• Chemical Name: (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
• CAS No.: 851889-76-4
• Molecular Formula: C₃₆H₆₂O₆Si₂
• Molecular Weight: 647.056
• Mol file: 851889-76-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 20 articles about (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 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%

(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 (851889-75-3) → (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 (851889-77-5) + (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 (851889-76-4)

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:

(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester (851889-68-4) → (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 (851889-76-4)

Guidance literature:

Multi-step reaction with 5 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

5.1: PPTS / CH₂Cl₂

With pyridine; potassium hydroxide; samarium diiodide; pyridinium p-toluenesulfonate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 3.1: Evans-Tischenko reduction;

DOI:10.1021/ja043168j

Reference yield:

(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 (851889-73-1) → (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 (851889-76-4)

Guidance literature:

Multi-step reaction with 3 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

3.1: PPTS / CH₂Cl₂

With potassium hydroxide; samarium diiodide; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Evans-Tischenko reduction;

DOI:10.1021/ja043168j

upstream raw materials:

(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

(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

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

(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

Downstream raw materials:

(R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z)-(2S,5S,6S,7S)-6-Hydroxy-9-iodo-2-methoxymethoxy-5,7-dimethyl-deca-3,8-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester

(2R,3S,4S,5S,7S,8Z,10S,11S,12S,13Z)-14-iodo-3,5-[(S)-4-methoxybenzilidenedioxy]-7,11-bis-methoxymethoxy-2,4,10,12-tetramethylpentadeca-8,13-dienoic acid methyl ester

(2R,3S,4S,5S,7S,8Z,10S,11S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-14-iodo-3,5-[(S)-4-methoxybenzilidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethylpentadeca-8,13-dienoic acid methyl ester

(2R,3S,4S,5S,7S,10S,11S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-hydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester