methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate

Base Information

Chemical Name:methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate
CAS No.:1585180-71-7
Molecular Formula:C₂₃H₃₈O₅
Molecular Weight:394.552
Hs Code.:

Synonyms:methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate

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Chemical Property of methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate

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Technology Process of methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate

There total 13 articles about methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate 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: 81.0%

: 31469-15-5
1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

: 676324-77-9
(3R,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptanal

: 1585180-71-7
methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate

Guidance literature:: With C₁₂H₁₆BNO₄S; N-((4-methylphenyl)sulfonyl)-D-valine; borane; In tetrahydrofuran; at -78 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jm4019965

Reference yield:

: 197454-20-9
(S)-5,5-dimethyl-4-hydroxyhexan-2-one

: 1585180-71-7
methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 0.67 h / 0 °C / Inert atmosphere

3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

4.1: potassium tert-butylate / toluene / 1 h / Reflux; Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Molecular sieve

6.1: triethylamine / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

7.1: titanium(IV) isopropylate / dichloromethane / 1 h / Inert atmosphere; Reflux

7.2: 4 h / Inert atmosphere; Reflux

8.1: copper(l) cyanide / diethyl ether / 2.33 h / -78 °C / Inert atmosphere

8.2: 2.33 h / -78 - -20 °C

9.1: trimethylaluminum / dichloromethane; Hexachlorobutadiene / -78 - 20 °C / Inert atmosphere

10.1: trifluorormethanesulfonic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 °C / Inert atmosphere

12.1: N-((4-methylphenyl)sulfonyl)-D-valine; borane; C₁₂H₁₆BNO₄S / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; trifluorormethanesulfonic acid; C₁₂H₁₆BNO₄S; N-((4-methylphenyl)sulfonyl)-D-valine; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; trimethylaluminum; copper(l) cyanide; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; Hexachlorobutadiene; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm4019965

Reference yield:

: 630-19-3
pivalaldehyde

: 1585180-71-7
methyl (3S,5S,7S)-3-hydroxy-7-(4-methoxybenzyloxy)-2,2,5,8,8-pentamethylnonanoate

Guidance literature:: Multi-step reaction with 13 steps

1.1: D-Prolin / acetone; dimethyl sulfoxide / 97 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / methanol / 0.67 h / 0 °C / Inert atmosphere

4.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

5.1: potassium tert-butylate / toluene / 1 h / Reflux; Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Molecular sieve

7.1: triethylamine / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

8.1: titanium(IV) isopropylate / dichloromethane / 1 h / Inert atmosphere; Reflux

8.2: 4 h / Inert atmosphere; Reflux

9.1: copper(l) cyanide / diethyl ether / 2.33 h / -78 °C / Inert atmosphere

9.2: 2.33 h / -78 - -20 °C

10.1: trimethylaluminum / dichloromethane; Hexachlorobutadiene / -78 - 20 °C / Inert atmosphere

11.1: trifluorormethanesulfonic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

12.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 °C / Inert atmosphere

13.1: N-((4-methylphenyl)sulfonyl)-D-valine; borane; C₁₂H₁₆BNO₄S / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; trifluorormethanesulfonic acid; C₁₂H₁₆BNO₄S; N-((4-methylphenyl)sulfonyl)-D-valine; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; trimethylaluminum; copper(l) cyanide; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; D-Prolin; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; Hexachlorobutadiene; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jm4019965