(rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone

Base Information

Chemical Name:(rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone
CAS No.:266675-29-0
Molecular Formula:C₂₁H₃₁NO₃Si
Molecular Weight:373.568
Hs Code.:

Synonyms:(rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone

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Chemical Property of (rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone

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Technology Process of (rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone

There total 1 articles about (rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone 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: 71.0%

: 88023-78-3
para-methoxybenzyl chloride

: 81355-48-8
1-tert-butyldimethylsilyl-4-propargyl-2-azetidinone

: 266675-29-0
(rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone

Guidance literature:: 1-tert-butyldimethylsilyl-4-propargyl-2-azetidinone; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

para-methoxybenzyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 4h; Further stages.;
DOI:10.1002/(sici)1099-0690(200003)2000:6<939::aid-ejoc939>3.0.co;2-q

Reference yield: 75.0%

: 266675-30-3
1-bromo-4-[(4-methoxyphenyl)methoxy]but-2-yne

: 266675-29-0
(rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone

: (3R*,4R*)-1-(tert-butyldimethylsilyl)-3,4-bis{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone

Guidance literature:: (rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

1-bromo-4-[(4-methoxyphenyl)methoxy]but-2-yne; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 2.33333h; Further stages.;
DOI:10.1002/(sici)1099-0690(200003)2000:6<939::aid-ejoc939>3.0.co;2-q

Reference yield:

: 266675-29-0
(rac)-1-(tert-butyldimethylsilyl)-4-{4-[(4-methoxyphenyl)methoxy]but-2-yn-1-yl}-2-azetidinone

: C₃₁H₃₉NO₇S₂Si

Guidance literature:: Multi-step reaction with 3 steps

1.1: i-Pr₂NLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: 75 percent / tetrahydrofuran; hexane / 2.33 h / -78 - 0 °C

2.1: 87 percent / dichlorodicyano-p-benzoquinone / 2-methyl-propan-2-ol; aq. phosphate buffer / 13 h / 20 °C / pH 7

3.1: 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h / -20 - 20 °C

With dmap; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; phosphate buffer; hexane; dichloromethane; tert-butyl alcohol; 1.1: Metallation / 1.2: Substitution / 2.1: Oxidation / 3.1: Tosylation;
DOI:10.1002/(sici)1099-0690(200003)2000:6<939::aid-ejoc939>3.0.co;2-q