11-Dodecynoic acid, 10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (4R,10R)-

Base Information

Chemical Name:11-Dodecynoic acid, 10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (4R,10R)-
CAS No.:837428-43-0
Molecular Formula:C36H62O4Si2
Molecular Weight:615.057
Hs Code.:

11-Dodecynoic acid,
10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]-,
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester,
(4R,10R)-

Synonyms:

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Chemical Property of 11-Dodecynoic acid, 10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (4R,10R)-

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Technology Process of 11-Dodecynoic acid, 10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (4R,10R)-

There total 17 articles about 11-Dodecynoic acid, 10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (4R,10R)- 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: 75.0%

: 1066-54-2
trimethylsilylacetylene

: 837428-42-9
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (4R)-10-oxo-4-[2-(trimethylsilyl)ethoxy]decanoate

: 837428-43-0
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (4R,10R)-10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]dodec-11-ynoate

Guidance literature:: With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 60 ℃; for 20h;
DOI:10.1021/ol0479242

Reference yield:

: 100-73-2
acrolein dimer

: 837428-43-0
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (4R,10R)-10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]dodec-11-ynoate

Guidance literature:: Multi-step reaction with 9 steps

1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 7 h / -78 °C

2: 81 percent / p-toluenesulfonic acid monohydrate; water / tetrahydrofuran / 20 h / 32 °C

3: LiHMDS / toluene; tetrahydrofuran / 14 h / 0 °C

4: 91 percent / imidazole; DMAP / 1,2-dichloro-ethane; tetrahydrofuran / 16 h / 60 °C

5: neocuproine / Pd₂(dba)3 / CH₂Cl₂ / 3 h / 20 °C

6: 90 percent / hydrogen / Pd on activated carbon / hexane / 48 h / 20 °C

7: 100 percent / BH₃*DMS / tetrahydrofuran; CH₂Cl₂ / 12 h / 20 °C

8: 82 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4 h / 0 °C

9: 75 percent / zinc triflate; triethylamine; (1R,2S)-N-(+)-methylephedrine / toluene / 20 h / 60 °C

With pyridine; 1H-imidazole; dmap; 2.9-dimethyl-1,10-phenanthroline; 18-crown-6 ether; dimethylsulfide borane complex; (-)-N-methylephedrine; water; hydrogen; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; toluene; 3: Horner-Wadsworth-Emmons reaction / 8: Dess-Martin oxidation;
DOI:10.1021/ol0479242

Reference yield:

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 837428-43-0
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (4R,10R)-10-hydroxy-12-(trimethylsilyl)-4-[2-(trimethylsilyl)ethoxy]dodec-11-ynoate

Guidance literature:: Multi-step reaction with 5 steps

1: neocuproine / Pd₂(dba)3 / CH₂Cl₂ / 3 h / 20 °C

2: 90 percent / hydrogen / Pd on activated carbon / hexane / 48 h / 20 °C

3: 100 percent / BH₃*DMS / tetrahydrofuran; CH₂Cl₂ / 12 h / 20 °C

4: 82 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4 h / 0 °C

5: 75 percent / zinc triflate; triethylamine; (1R,2S)-N-(+)-methylephedrine / toluene / 20 h / 60 °C

With pyridine; 2.9-dimethyl-1,10-phenanthroline; dimethylsulfide borane complex; (-)-N-methylephedrine; hydrogen; zinc trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; toluene; 4: Dess-Martin oxidation;
DOI:10.1021/ol0479242