(3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one

Base Information

Chemical Name:(3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one
CAS No.:900171-35-9
Molecular Formula:C₂₃H₃₈O₅Si
Molecular Weight:422.637
Hs Code.:

Synonyms:(3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one

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Chemical Property of (3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one

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Technology Process of (3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one

There total 6 articles about (3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one 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: 91.0%

: 79-03-8
propionyl chloride

: 500220-30-4
(2S,3R)-3-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpentanal

: 900171-35-9
(3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one

Guidance literature:: With (1S,2R,4S,5R)-2-[(S)-(6-methoxyquinolin-4-yl)((trimethylsilyl)oxy)methyl]-5-vinylquinuclidine; N-ethyl-N,N-diisopropylamine; lithium iodide; In diethyl ether; dichloromethane; at -78 ℃;
DOI:10.1021/ja061938g

Reference yield:

: 900171-30-4
(3S,4R)-4-[2-(4-methoxybenzyloxy)ethyl]-3-methyloxetan-2-one

: 900171-35-9
(3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: dimethylaluminum chloride / CH₂Cl₂; hexane / 2 h / -25 °C

2: imidazole; DMAP / dimethylformamide / 20 h / 20 °C

3: 96 percent / tBu₂AlH / tetrahydrofuran; hexane / 0.5 h / -50 °C

4: 91 percent / LiI; O-trimethylsilylquinine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / -78 °C

With 1H-imidazole; dmap; (1S,2R,4S,5R)-2-[(S)-(6-methoxyquinolin-4-yl)((trimethylsilyl)oxy)methyl]-5-vinylquinuclidine; dimethylaluminum chloride; di(tert-butyl)aluminium hydride; N-ethyl-N,N-diisopropylamine; lithium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja061938g

Reference yield:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 900171-35-9
(3R,4S)-4-[(2S,3R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-3-methyloxetan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / LiClO₄; O-trimethylsilylquinidine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / 18 h / -78 °C

2: dimethylaluminum chloride / CH₂Cl₂; hexane / 2 h / -25 °C

3: imidazole; DMAP / dimethylformamide / 20 h / 20 °C

4: 96 percent / tBu₂AlH / tetrahydrofuran; hexane / 0.5 h / -50 °C

5: 91 percent / LiI; O-trimethylsilylquinine; N,N-diisopropylethylamine / CH₂Cl₂; diethyl ether / -78 °C

With 1H-imidazole; dmap; 2-((1S)-(6-methoxyquinolin-4-yl)((trimethylsilyl)oxy)methyl)5-vinylquinuclidine; (1S,2R,4S,5R)-2-[(S)-(6-methoxyquinolin-4-yl)((trimethylsilyl)oxy)methyl]-5-vinylquinuclidine; lithium perchlorate; dimethylaluminum chloride; di(tert-butyl)aluminium hydride; N-ethyl-N,N-diisopropylamine; lithium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja061938g