(2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid

Base Information

• Chemical Name: (2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid
• CAS No.: 1303438-60-9
• Molecular Formula: C₃₂H₄₈O₁₀
• Molecular Weight: 592.727

Synonyms:(2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid

Chemical Property of (2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid

There total 17 articles about (2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid 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:

C32H48O9 → (2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid (1303438-60-9)

Guidance literature:

With sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogen phosphate; In water; tert-butyl alcohol; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo2003506

Reference yield:

(1S,6R,8R)-8-Vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide (887143-81-9) → (2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid (1303438-60-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: Hoveyda-Grubbs catalyst second generation / 1,1-dichloroethane / 90 °C / Inert atmosphere

2.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / 1,2-dichloro-ethane / Inert atmosphere

3.1: formic acid; palladium diacetate; triethylamine / 1,2-dichloro-ethane / 40 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere

6.1: pyridine; ozone / methanol; dichloromethane / -78 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: magnesium / diethyl ether / -78 °C / Inert atmosphere

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / Inert atmosphere

9.1: cerium(III) chloride heptahydrate / water; acetonitrile / Inert atmosphere

10.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / -78 °C / Inert atmosphere

11.1: pyridine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

13.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

14.1: sodium chlorite; sodium dihydrogen phosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium chlorite; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; Hoveyda-Grubbs catalyst second generation; 2-methyl-but-2-ene; oxalyl dichloride; cerium(III) chloride heptahydrate; sodium dihydrogen phosphate; diethyl methoxy borane; 2-nitrobenzenesulfonyl hydrazide; tetrabutyl ammonium fluoride; palladium diacetate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; 1,1-dichloroethane; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; 13.1: Swern oxidation;

DOI:10.1021/jo2003506

Reference yield:

(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 (1003890-41-2) → (2S,3S,4R,7S,9R,11S)-7,9,11-triacetoxy-3-(4-methoxybenzyloxy)-2,4,14-trimethylpentadec-14-enoic acid (1303438-60-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: formic acid; palladium diacetate; triethylamine / 1,2-dichloro-ethane / 40 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere

4.1: pyridine; ozone / methanol; dichloromethane / -78 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: magnesium / diethyl ether / -78 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / Inert atmosphere

7.1: cerium(III) chloride heptahydrate / water; acetonitrile / Inert atmosphere

8.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / -78 °C / Inert atmosphere

9.1: pyridine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

11.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

12.1: sodium chlorite; sodium dihydrogen phosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium chlorite; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; 2-methyl-but-2-ene; oxalyl dichloride; cerium(III) chloride heptahydrate; sodium dihydrogen phosphate; diethyl methoxy borane; tetrabutyl ammonium fluoride; palladium diacetate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; 11.1: Swern oxidation;

DOI:10.1021/jo2003506

upstream raw materials:

(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

C₂₉H₅₁O₇PSi

Downstream raw materials:

(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

(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

(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)-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

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