(5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate

Base Information

• Chemical Name: (5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate
• CAS No.: 1303438-79-0
• Molecular Formula: C₅₄H₈₆O₁₃
• Molecular Weight: 943.269
• Mol file: 1303438-79-0.mol

Synonyms:(5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate

Chemical Property of (5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate

There total 36 articles about (5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate 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: 94.0%

(5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-5-methyl-7-(triethylsilyloxy)dec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate (1303438-68-7) → (5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate (1303438-79-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.75h; Inert atmosphere;

DOI:10.1021/jo2003506

Reference yield:

(R)-2-((4S,6R)-6-(5-(4-methoxybenzyloxy)pentyl)-2,2-dimethyl-1,3-dioxan-4-yl)propan-1-ol (1303438-61-0) → (5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate (1303438-79-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1H-imidazole; dmap / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate / ethyl acetate / 10 h / 20 °C

3.1: 1H-imidazole; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

6.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere

7.1: tert.-butyl lithium / diethyl ether; pentane / 0.42 h / -78 - 0 °C / Inert atmosphere

7.2: 1 h / -78 °C / Inert atmosphere

8.1: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 23.5 h / -78 - -30 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene; pentane; 6.1: Swern oxidation;

DOI:10.1021/jo2003506

Reference yield:

(4S,6S)-4,6-diethenyl-2-(2-propen-1-yloxy)-1,3,2-dioxaphosphorinane 2-oxide (862973-37-3) → (5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-7-hydroxy-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate (1303438-79-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane

2.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 90 °C / Inert atmosphere

3.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / dichloromethane / Inert atmosphere

4.1: copper(I) cyanide di(lithium chloride) / tetrahydrofuran / -30 - 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: pyridinium p-toluenesulfonate / dichloromethane / 20 °C / Inert atmosphere

6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere

6.2: 3408 / 2 h / pH 7 / Inert atmosphere

7.1: sodium tetrahydroborate / ethanol / 0.75 h / 0 - 20 °C / Inert atmosphere

8.1: 1H-imidazole; dmap / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate / ethyl acetate / 10 h / 20 °C

10.1: 1H-imidazole; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere

10.2: 0 °C / Inert atmosphere

11.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

13.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere

14.1: tert.-butyl lithium / diethyl ether; pentane / 0.42 h / -78 - 0 °C / Inert atmosphere

14.2: 1 h / -78 °C / Inert atmosphere

15.1: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 23.5 h / -78 - -30 °C / Inert atmosphere

16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; copper(I) cyanide di(lithium chloride); 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; 2-nitrobenzenesulfonyl hydrazide; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; pentane; 13.1: Swern oxidation;

DOI:10.1021/jo2003506

upstream raw materials:

(4S,6S)-4,6-diethenyl-2-(2-propen-1-yloxy)-1,3,2-dioxaphosphorinane 2-oxide

(1S,6R,8R)-8-Vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide

(4R,6R)-2-Allyloxy-4,6-divinyl-[1,3,2]dioxaphosphinane 2-oxide

(1R,6R,8S)-8-((3R,4S,5R)-6-((tert-butyldimethylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,5-dimethylhexyl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide

Downstream raw materials:

(5S,7R,9S,12R,13S,14S)-15-((4R,8R,9S,10S,12R,E)-4-acetoxy-10,12-dihydroxy-6,9-dimethylheptadeca-6,16-dien-8-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate

(5S,7R,9S,12R,13S,14S)-15-((2S,3R,7R,E)-7-acetoxy-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-5-methyldec-4-en-3-yloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethyl-15-oxopentadec-1-ene-5,7,9-triyl triacetate