(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

Base Information

• Chemical Name: (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
• CAS No.: 851889-82-2
• Molecular Formula: C₃₆H₅₉IO₈Si
• Molecular Weight: 774.85
• Mol file: 851889-82-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 25 articles about (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 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:

(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester (851889-68-4) → (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 (851889-82-2)

Guidance literature:

Multi-step reaction with 11 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

6.1: 0.47 g / RuCl₂(PPh₃)3 / benzene / 8 h / 20 °C

7.1: NaClO₂; NaH₂PO₄*H₂₀; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

8.1: 0.44 g / benzene; methanol; hexane / 0.25 h

9.1: 83 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

10.1: H₂; quinoline / Pd/CaCO₃/Pb / hexane / 8 h / 760 Torr

11.1: 0.397 g / N-iodosuccinimide / acetonitrile; various solvent(s) / 3 h

With pyridine; quinoline; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; hydrogen; pyridinium p-toluenesulfonate; ozone; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; tert-butyl alcohol; benzene; 3.1: Evans-Tischenko reduction / 10.1: Lindlar reduction / 11.1: Kishi iododesilylation;

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) → (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 (851889-82-2)

Guidance literature:

Multi-step reaction with 9 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

4.1: 0.47 g / RuCl₂(PPh₃)3 / benzene / 8 h / 20 °C

5.1: NaClO₂; NaH₂PO₄*H₂₀; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

6.1: 0.44 g / benzene; methanol; hexane / 0.25 h

7.1: 83 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

8.1: H₂; quinoline / Pd/CaCO₃/Pb / hexane / 8 h / 760 Torr

9.1: 0.397 g / N-iodosuccinimide / acetonitrile; various solvent(s) / 3 h

With quinoline; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; hydrogen; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; tert-butyl alcohol; benzene; 1.1: Evans-Tischenko reduction / 8.1: Lindlar reduction / 9.1: Kishi iododesilylation;

DOI:10.1021/ja043168j

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (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 (851889-82-2)

Guidance literature:

Multi-step reaction with 12 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

5.1: KOH / methanol / 20 °C

5.2: 20 percent / silica gel / methanol; hexane

6.1: PPTS / CH₂Cl₂

7.1: 0.47 g / RuCl₂(PPh₃)3 / benzene / 8 h / 20 °C

8.1: NaClO₂; NaH₂PO₄*H₂₀; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

9.1: 0.44 g / benzene; methanol; hexane / 0.25 h

10.1: 83 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

11.1: H₂; quinoline / Pd/CaCO₃/Pb / hexane / 8 h / 760 Torr

12.1: 0.397 g / N-iodosuccinimide / acetonitrile; various solvent(s) / 3 h

With pyridine; quinoline; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; hydrogen; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 4.1: Evans-Tischenko reduction / 11.1: Lindlar reduction / 12.1: Kishi iododesilylation;

DOI:10.1021/ja043168j

upstream raw materials:

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

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

(R)-2-[(2S,4S,5S,6S)-6-[(Z)-(2S,5S,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,7-dimethyl-9-trimethylsilanyl-dec-8-en-3-ynyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde

(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

Downstream raw materials:

(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

(R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13S,14S,15S)-14-Carbamoyloxy-12-hydroxy-2,6-bis-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl)-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,16S,17R,18S,19S,20S,21Z)-19-hydroxy-3,5-[(S)-4-methoxybenzilidenedioxy]-7,11-bis-methoxymethoxy-17-(4-methoxyphenoxyphenoxy)-2,4,10,12,14,16,18,20-octamethyltetracosa-8,13,21,23-tetraenoic acid methyl ester

2-[6-[14-carbamoyloxy-12-(4-methoxy-benzyloxy)-2,6-bis-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester