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

Base Information

• Chemical Name: 2-[6-[12-(4-methoxy-benzyloxy)-2,6-bis-methoxymethoxy-5,7,9,11,13,15-hexamethyl-14-triethylsilanyloxy-nonadeca-3,8,16,18-tetraenyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester
• CAS No.: 851889-85-5
• Molecular Formula: C₅₉H₉₄O₁₂Si
• Molecular Weight: 1023.47
• Mol file: 851889-85-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 41 articles about 2-[6-[12-(4-methoxy-benzyloxy)-2,6-bis-methoxymethoxy-5,7,9,11,13,15-hexamethyl-14-triethylsilanyloxy-nonadeca-3,8,16,18-tetraenyl]-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: 64.0%

(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 (851889-66-2) + (2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene (216669-69-1) → 2-[6-[12-(4-methoxy-benzyloxy)-2,6-bis-methoxymethoxy-5,7,9,11,13,15-hexamethyl-14-triethylsilanyloxy-nonadeca-3,8,16,18-tetraenyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester (851889-85-5)

Guidance literature:

(2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h;

With zinc(II) chloride; In tetrahydrofuran; pentane; at -78 - 0 ℃;

(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; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pentane; at 0 - 20 ℃; for 7h;

DOI:10.1021/ja043168j

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → 2-[6-[12-(4-methoxy-benzyloxy)-2,6-bis-methoxymethoxy-5,7,9,11,13,15-hexamethyl-14-triethylsilanyloxy-nonadeca-3,8,16,18-tetraenyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester (851889-85-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 4.8 g / p-toluenesulfonic acid / dimethylformamide / 5 h / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

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

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

4.1: diethyl ether / 48 h / 20 °C

5.1: 5.6 g / NaH / tetrahydrofuran / 3 h / 20 °C

6.1: 83 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / -78 - -50 °C

7.1: 95 percent / triphenylphosphine; I₂ / CH₂Cl₂ / 0 - 20 °C

8.1: t-BuLi / diethyl ether; pentane / 0.05 h / -78 °C

8.2: tetrahydrofuran; diethyl ether; pentane / 1.17 h / -78 - 20 °C

9.1: 50.0 mg / PdCl₂(dppf); TlOEt / dimethylformamide; tetrahydrofuran / 14 h / 20 °C

With pyridine; 2,6-dimethylpyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; iodine; tert.-butyl lithium; thallium (I) ethoxide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; pentane; 5.1: Peterson elimination / 9.1: Suzuki cross-coupling;

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) → 2-[6-[12-(4-methoxy-benzyloxy)-2,6-bis-methoxymethoxy-5,7,9,11,13,15-hexamethyl-14-triethylsilanyloxy-nonadeca-3,8,16,18-tetraenyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester (851889-85-5)

Guidance literature:

Multi-step reaction with 14 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

12.1: TBAF; AcOH / tetrahydrofuran / 36 h / 20 °C

13.1: 0.054 g / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

14.1: 50.0 mg / PdCl₂(dppf); TlOEt / dimethylformamide; tetrahydrofuran / 14 h / 20 °C

With pyridine; quinoline; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; hydrogen; thallium (I) ethoxide; pyridinium p-toluenesulfonate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 3.1: Evans-Tischenko reduction / 10.1: Lindlar reduction / 11.1: Kishi iododesilylation / 14.1: Suzuki cross-coupling;

DOI:10.1021/ja043168j

upstream 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

(2R,3S,4S,5S,6S,7Z)-1-iodo-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-diene

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

(3E,5S,6S,7R,8R,9S)-6-hydroxy-8,10-[(R)-4-methoxybenzilidenedioxy]-5,7,9-trimethyldec-3-enoic acid methyl ester

Downstream raw materials:

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

(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