Nonanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-2, 5,8,8-tetramethyl-, (2S,3S,5R,7S)-

Base Information

• Chemical Name: Nonanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-2, 5,8,8-tetramethyl-, (2S,3S,5R,7S)-
• CAS No.: 676324-84-8
• Molecular Formula: C27H48O4Si
• Molecular Weight: 464.761

Synonyms:

Chemical Property of Nonanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-2, 5,8,8-tetramethyl-, (2S,3S,5R,7S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Nonanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-2, 5,8,8-tetramethyl-, (2S,3S,5R,7S)-

There total 10 articles about Nonanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-2, 5,8,8-tetramethyl-, (2S,3S,5R,7S)- 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:

(3S)-2,2-dimethyl-5-hexen-3-ol (67760-86-5) → (2S,3S,5R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,5,8,8-tetramethyl-nonanal (676324-84-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 95 percent / sodium hydride / tetrahydrofuran / 12 h / 20 °C

2.1: N-methylmorpholine N-oxide; methanesulfonamide / osmium tetroxide / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

3.1: 1.17 g / sodium periodate on silica gel / CH₂Cl₂ / 0.5 h / 20 °C

4.1: KHMDS; HMPA / tetrahydrofuran; toluene / -70 - 20 °C

4.2: 69 percent / tetrahydrofuran; toluene / 16 h / -70 °C

5.1: copper(I) bromide-dimethyl sulfide complex / tetrahydrofuran; various solvent(s); diethyl ether / 1 h / -40 °C

5.2: 92 percent / tetrahydrofuran; various solvent(s); diethyl ether / -78 - 20 °C

6.1: (CH₃)3Al / CH₂Cl₂; hexane / cooling

6.2: 36 percent / CH₂Cl₂; hexane / -30 - 20 °C

7.1: 92 percent / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

8.1: potassium tert-butoxide; n-butyllithium / tetrahydrofuran; hexane / -78 - -45 °C

8.2: (+)-B-(methoxy)diisopinocampheylborane / tetrahydrofuran; hexane / 1 h / -78 °C

8.3: 53 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12.5 h / -100 - -78 °C

9.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

10.1: 256 mg / N-methylmorpholine N-oxide; methanesulfonamide / osmium tetroxide / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

11.1: sodium periodate on silica gel / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; n-butyllithium; copper(I) bromide dimethylsulfide complex; methanesulfonamide; potassium tert-butylate; trimethylaluminum; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 4.2: Wadsworth-Emmons condensation;

DOI:10.1016/j.tetasy.2003.11.026

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (2S,3S,5R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,5,8,8-tetramethyl-nonanal (676324-84-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 95 percent / sodium hydride / tetrahydrofuran / 12 h / 20 °C

2.1: N-methylmorpholine N-oxide; methanesulfonamide / osmium tetroxide / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

3.1: 1.17 g / sodium periodate on silica gel / CH₂Cl₂ / 0.5 h / 20 °C

4.1: KHMDS; HMPA / tetrahydrofuran; toluene / -70 - 20 °C

4.2: 69 percent / tetrahydrofuran; toluene / 16 h / -70 °C

5.1: copper(I) bromide-dimethyl sulfide complex / tetrahydrofuran; various solvent(s); diethyl ether / 1 h / -40 °C

5.2: 92 percent / tetrahydrofuran; various solvent(s); diethyl ether / -78 - 20 °C

6.1: (CH₃)3Al / CH₂Cl₂; hexane / cooling

6.2: 36 percent / CH₂Cl₂; hexane / -30 - 20 °C

7.1: 92 percent / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

8.1: potassium tert-butoxide; n-butyllithium / tetrahydrofuran; hexane / -78 - -45 °C

8.2: (+)-B-(methoxy)diisopinocampheylborane / tetrahydrofuran; hexane / 1 h / -78 °C

8.3: 53 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12.5 h / -100 - -78 °C

9.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

10.1: 256 mg / N-methylmorpholine N-oxide; methanesulfonamide / osmium tetroxide / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

11.1: sodium periodate on silica gel / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; n-butyllithium; copper(I) bromide dimethylsulfide complex; methanesulfonamide; potassium tert-butylate; trimethylaluminum; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 4.2: Wadsworth-Emmons condensation;

DOI:10.1016/j.tetasy.2003.11.026

Reference yield:

(4S)-4-(para-methoxybenzyloxy)-5,5-dimethyl-1-hexene (676324-83-7) → (2S,3S,5R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,5,8,8-tetramethyl-nonanal (676324-84-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: N-methylmorpholine N-oxide; methanesulfonamide / osmium tetroxide / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

2.1: 1.17 g / sodium periodate on silica gel / CH₂Cl₂ / 0.5 h / 20 °C

3.1: KHMDS; HMPA / tetrahydrofuran; toluene / -70 - 20 °C

3.2: 69 percent / tetrahydrofuran; toluene / 16 h / -70 °C

4.1: copper(I) bromide-dimethyl sulfide complex / tetrahydrofuran; various solvent(s); diethyl ether / 1 h / -40 °C

4.2: 92 percent / tetrahydrofuran; various solvent(s); diethyl ether / -78 - 20 °C

5.1: (CH₃)3Al / CH₂Cl₂; hexane / cooling

5.2: 36 percent / CH₂Cl₂; hexane / -30 - 20 °C

6.1: 92 percent / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

7.1: potassium tert-butoxide; n-butyllithium / tetrahydrofuran; hexane / -78 - -45 °C

7.2: (+)-B-(methoxy)diisopinocampheylborane / tetrahydrofuran; hexane / 1 h / -78 °C

7.3: 53 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12.5 h / -100 - -78 °C

8.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

9.1: 256 mg / N-methylmorpholine N-oxide; methanesulfonamide / osmium tetroxide / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

10.1: sodium periodate on silica gel / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; n-butyllithium; copper(I) bromide dimethylsulfide complex; methanesulfonamide; potassium tert-butylate; trimethylaluminum; potassium hexamethylsilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 3.2: Wadsworth-Emmons condensation;

DOI:10.1016/j.tetasy.2003.11.026

upstream raw materials:

(3S)-2,2-dimethyl-5-hexen-3-ol

p-Methoxybenzyl bromide

(4R,6S)-6-tert-butyl-4-methyltetrahydro-2H-pyran-2-one

(4S)-4-(para-methoxybenzyloxy)-5,5-dimethyl-1-hexene

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