3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

Base Information

Chemical Name:3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one
CAS No.:90628-93-6
Molecular Formula:C₁₉H₂₉NO₃SSi
Molecular Weight:379.596
Hs Code.:

Synonyms:3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

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Chemical Property of 3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

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Technology Process of 3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

There total 32 articles about 3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-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: 66.0%

: 102679-25-4
(3S,4R)-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

: 90628-93-6
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

Guidance literature:: With ammonium cerium(IV) nitrate;
DOI:10.1016/S0040-4039(00)88946-7

Reference yield:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 90628-93-6
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

2: 1) trimethylsilyl trifluoromethanesulfonate

With triethylamine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran;
DOI:10.1016/S0040-4039(01)81292-2

Reference yield:

: 99765-25-0
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

: 90628-93-6
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 58.7 percent / acetic acid, KMnO₄ / acetone; H₂O / 24 h

2: 1.) ethylmagnesium bromide / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h

3: 1.) trifluoroacetic acid, 2.) H₂O / 1.) methylene chloride, RT, 30 min, 2.) AcOEt, RT, 5 min

With potassium permanganate; ethylmagnesium bromide; water; acetic acid; trifluoroacetic acid; In water; acetone;
DOI:10.1021/jo00353a025