{(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester

Base Information

• Chemical Name: {(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester
• CAS No.: 865540-28-9
• Molecular Formula: C₄₂H₅₇O₁₁P
• Molecular Weight: 768.882
• Mol file: 865540-28-9.mol

Synonyms:{(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester

Chemical Property of {(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester

There total 19 articles about {(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl 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: 91.0%

(3S,4R,5S)-5-(4-Methoxy-benzyloxy)-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-3-methyl-oct-7-enoic acid methyl ester (865540-51-8) + dimethyl methane phosphonate (756-79-6) → {(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester (865540-28-9)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(3S,4R,5S)-5-(4-Methoxy-benzyloxy)-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-3-methyl-oct-7-enoic acid methyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/ol051543m

Reference yield:

(2S,3R,4S)-4-Benzyloxy-2-methyl-hept-6-ene-1,3-diol (865540-44-9) → {(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester (865540-28-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 96 percent / imidazole / dimethylformamide / 20 h / 70 °C

2.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.17 h / 0 °C

2.2: 81 percent / tetrahydrofuran; various solvent(s) / 0 - 20 °C

3.1: triethylamine / tetrahydrofuran / -78 - 0 °C

4.1: 71 percent / n-BuLi / tetrahydrofuran; hexane; CH₂Cl₂ / 1 h / -78 °C

5.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / -78 - -40 °C

5.2: 50 percent / CH₂Cl₂ / 0.33 h / -78 °C

6.1: lithium borohydride / diethyl ether; methanol; tetrahydrofuran / 1 h / 0 °C

7.1: 0.901 g / sodium; naphthalene / tetrahydrofuran / 0 °C

8.1: sodium hydride / dimethylformamide; various solvent(s) / 0 - 20 °C

9.1: 0.801 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

10.1: 85 percent / imidazole; triphenylphosphine; iodine / benzene / 1 h / 20 °C

11.1: 91 percent / dimethylsulfoxide / 15 h

12.1: 85 percent / KOH; H₂O / ethanol / 168 h / Heating

13.1: 95 percent / anhydrous K₂CO₃ / dimethylformamide / 0.5 h / 20 °C

14.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

14.2: 91 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; potassium hydroxide; lithium borohydride; n-butyllithium; naphthalene; tetrabutyl ammonium fluoride; water; iodine; sodium; titanium tetrachloride; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; (-)-sparteine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ol051543m

Reference yield:

(2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol (865540-24-5) → {(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester (865540-28-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.17 h / 0 °C

1.2: 81 percent / tetrahydrofuran; various solvent(s) / 0 - 20 °C

2.1: triethylamine / tetrahydrofuran / -78 - 0 °C

3.1: 71 percent / n-BuLi / tetrahydrofuran; hexane; CH₂Cl₂ / 1 h / -78 °C

4.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / -78 - -40 °C

4.2: 50 percent / CH₂Cl₂ / 0.33 h / -78 °C

5.1: lithium borohydride / diethyl ether; methanol; tetrahydrofuran / 1 h / 0 °C

6.1: 0.901 g / sodium; naphthalene / tetrahydrofuran / 0 °C

7.1: sodium hydride / dimethylformamide; various solvent(s) / 0 - 20 °C

8.1: 0.801 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

9.1: 85 percent / imidazole; triphenylphosphine; iodine / benzene / 1 h / 20 °C

10.1: 91 percent / dimethylsulfoxide / 15 h

11.1: 85 percent / KOH; H₂O / ethanol / 168 h / Heating

12.1: 95 percent / anhydrous K₂CO₃ / dimethylformamide / 0.5 h / 20 °C

13.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

13.2: 91 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; potassium hydroxide; lithium borohydride; n-butyllithium; naphthalene; tetrabutyl ammonium fluoride; water; iodine; sodium; titanium tetrachloride; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; (-)-sparteine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ol051543m

upstream raw materials:

(3S,4R,5S)-5-(4-Methoxy-benzyloxy)-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-3-methyl-oct-7-enoic acid methyl ester

dimethyl methane phosphonate

(2S,3R,4S)-4-Benzyloxy-2-methyl-hept-6-ene-1,3-diol

(2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

Downstream raw materials:

C₆₈H₉₈O₁₂Si

1-[3-hydroxy-7-(4-methoxy-benzyloxy)-3,5-dimethyl-8-triisopropylsilanyloxymethyl-oxocan-2-yl]-7-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-5-methyl-deca-1,9-dien-3-one