(3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one

Base Information

Chemical Name:(3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one
CAS No.:113494-93-2
Molecular Formula:C₃₆H₆₇NO₆Si₃
Molecular Weight:694.188
Hs Code.:

(3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one

Synonyms:(3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one

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Chemical Property of (3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one

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Technology Process of (3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one

There total 10 articles about (3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-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: 96.0%

: (3S,4S)-3-[(2S,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-methyl-butyl]-1-(tert-butyl-dimethyl-silanyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

: 113494-93-2
(3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one

Guidance literature:: With COCl₂; In dimethyl sulfoxide;
DOI:10.1039/c39870000992

Reference yield:

: 113494-89-6
methyl (S)-4-<(1,1-dimethylethyl)dimethylsiloxy>-3-hydroxybutanoate

: 113494-93-2
(3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) LDA, 2.) TMEDA / 1.) THF, -50 deg C -> -10 deg C, 2.) -70 deg C, 4 h

2: 92 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 60 h / Ambient temperature

3: 94 percent / DIBAL-H / tetrahydrofuran; hexane / -25 °C

4: 97 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 1.) -78 deg C, 5 min, 2.) -78 deg C -> room temperature

5: 1.) lithium diethylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 4 h

6: 96 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -78 °C

With dmap; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; lithium diethylamide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

Reference yield:

: 113494-91-0
(2R,3S)-3-benzyloxymethoxy-4-(tert-butyldimethylsilyloxy)-2-methylbutanal

: 113494-93-2
(3S,4S)-3-<(2'R,3'S)-3'-benzoyloxymethoxy-4'-(tert-butyldimethylsilyloxy)-2'-methyl-1'-oxobutyl>-1-(tert-butyldimethylsilyl)-4-(tert-butyldimethylsilyloxymethyl)-3-methylazetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) lithium diethylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 4 h

2: 96 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -78 °C

With oxalyl dichloride; lithium diethylamide; dimethyl sulfoxide; In dichloromethane;