1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-2-azetidinone

Base Information

Chemical Name:1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-2-azetidinone
CAS No.:109975-90-8
Molecular Formula:C₂₆H₄₄N₂O₆SSi₂
Molecular Weight:568.882
Hs Code.:

Synonyms:1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-2-azetidinone

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Chemical Property of 1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-2-azetidinone

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Technology Process of 1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-2-azetidinone

There total 8 articles about 1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-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: 83.0%

: 109975-89-5
1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-dihydroxy-4-nitro-4-(phenylthio)butyl>oxy>-2-azetidinone

: 109975-90-8
1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-2-azetidinone

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at -78 - -10 ℃; for 0.666667h;
DOI:10.1021/jo00230a008

Reference yield:

: 60595-16-6
(phenylthio)nitromethane

: 109975-90-8
1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-2-azetidinone

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) t-BuOK / 1.) THF, t-BuOH, 0 deg C, 2.) THF, t-BuOH, 0 deg C, 24 h

2: 83 percent / MeSO₂Cl, Et₃N / CH₂Cl₂ / 0.67 h / -78 - -10 °C

With potassium tert-butylate; methanesulfonyl chloride; triethylamine; In dichloromethane;
DOI:10.1021/jo00230a008

Reference yield:

: 109975-85-1
4-<(3-hydroxy-2-methylenepropyl)oxy>-2-azetidinone

: 109975-90-8
1-(tert-butyldimethylsilyl)-4-<<2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-hydroxy-4-nitro-4-(phenylthio)-3(Z)-butenyl>oxy>-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / ethyldiisopropylamine / CH₂Cl₂ / 12 h / Ambient temperature

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, reflux, 4 h

3: 95 percent / tetrahydrofuran / -78 - 0 °C

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, reflux, 18 h

5: 1.) t-BuOK / 1.) THF, t-BuOH, 0 deg C, 2.) THF, t-BuOH, 0 deg C, 24 h

6: 83 percent / MeSO₂Cl, Et₃N / CH₂Cl₂ / 0.67 h / -78 - -10 °C

With dimethylsulfide; potassium tert-butylate; ozone; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00230a008