(3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol

Base Information

Chemical Name:(3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol
CAS No.:144681-68-5
Molecular Formula:C₂₂H₃₈O₅Si
Molecular Weight:410.626
Hs Code.:

Synonyms:(3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol

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Chemical Property of (3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol

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Technology Process of (3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol

There total 5 articles about (3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol 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: 98.0%

: 410080-93-2
1-[(1S,2S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-(2-trimethylsilanyl-ethoxymethoxy)-but-3-enyloxymethyl]-4-methoxy-benzene

: 144681-68-5
(3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 16h;
DOI:10.1139/v01-133

Reference yield:

: 144681-67-4
3-(tert-butyldimethylsilanyloxy)-2,2-dimethylpropionaldehyde

: 144681-68-5
(3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: sec-BuLi; (+)-B-methoxydiisopinocampheylborane / hexane; tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

1.2: BF₃*OEt₂ / hexane; tetrahydrofuran; diethyl ether / -78 - -40 °C

1.3: 60 percent / HOCH₂CH₂NH₂; NaH / hexane; tetrahydrofuran; diethyl ether / 13 h / -40 - 20 °C

2.1: KN(SiMe₃)2 / tetrahydrofuran / 1.33 h / -78 - 0 °C

3.1: 98 percent / Bu₄NF / tetrahydrofuran / 16 h / 20 °C

With (+)-Ipc₂BOMe; tetrabutyl ammonium fluoride; sec.-butyllithium; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1139/v01-133

Reference yield:

: 126-30-7
2,2-Dimethyl-1,3-propanediol

: 144681-68-5
(3S,4S)-3-(4-methoxybenzyl)oxy-2,2-dimethyl-4-(2-trimethylsilylethoxy)methoxy-5-hexen-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 63 percent / imidazole / dimethylformamide / 16 h / 20 °C

2.1: 86 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - -10 °C

3.1: sec-BuLi; (+)-B-methoxydiisopinocampheylborane / hexane; tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

3.2: BF₃*OEt₂ / hexane; tetrahydrofuran; diethyl ether / -78 - -40 °C

3.3: 60 percent / HOCH₂CH₂NH₂; NaH / hexane; tetrahydrofuran; diethyl ether / 13 h / -40 - 20 °C

4.1: KN(SiMe₃)2 / tetrahydrofuran / 1.33 h / -78 - 0 °C

5.1: 98 percent / Bu₄NF / tetrahydrofuran / 16 h / 20 °C

With (+)-Ipc₂BOMe; 1H-imidazole; oxalyl dichloride; tetrabutyl ammonium fluoride; sec.-butyllithium; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 2.1: Swern oxidation;
DOI:10.1139/v01-133