(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene

Base Information

Chemical Name:(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene
CAS No.:676324-81-5
Molecular Formula:C₂₈H₅₀O₃Si
Molecular Weight:462.789
Hs Code.:

Synonyms:(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene

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Chemical Property of (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene

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Technology Process of (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene

There total 13 articles about (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene 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: 93.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 676324-80-4
(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-ol

: 676324-81-5
(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1016/j.tetasy.2003.11.026

Reference yield:

: 67760-86-5
(3S)-2,2-dimethyl-5-hexen-3-ol

: 676324-81-5
(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene

Guidance literature:: Multi-step reaction with 9 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

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:

: 2746-25-0
p-Methoxybenzyl bromide

: 676324-81-5
(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene

Guidance literature:: Multi-step reaction with 9 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

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