(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

Base Information

• Chemical Name: (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
• CAS No.: 851889-83-3
• Molecular Formula: C₃₉H₆₈O₈Si₂
• Molecular Weight: 721.135

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 24 articles about (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 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:

(2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester (851889-80-0) → (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 (851889-83-3)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In hexane; for 8h; under 760 Torr;

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) → (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 (851889-83-3)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; quinoline; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 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; tert-butyl alcohol; benzene; 3.1: Evans-Tischenko reduction / 10.1: Lindlar 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) → (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 (851889-83-3)

Guidance literature:

Multi-step reaction with 8 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

With quinoline; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 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; tert-butyl alcohol; benzene; 1.1: Evans-Tischenko reduction / 8.1: Lindlar reduction;

DOI:10.1021/ja043168j

upstream raw materials:

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

(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

(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

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