(3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

Base Information

Chemical Name:(3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one
CAS No.:162584-15-8
Molecular Formula:C₃₀H₅₃NO₆Si₂
Molecular Weight:579.925
Hs Code.:

(3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

Synonyms:(3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

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Chemical Property of (3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

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Technology Process of (3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

There total 6 articles about (3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-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: 85.0%

: 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

: 162584-15-8
(3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

Guidance literature:: With potassium fluoride; In methanol; at 0 ℃;

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 162584-15-8
(3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 60 h / Ambient temperature

2: 94 percent / DIBAL-H / tetrahydrofuran; hexane / -25 °C

3: 97 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 1.) -78 deg C, 5 min, 2.) -78 deg C -> room temperature

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

5: 96 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -78 °C

6: 85 percent / KF / methanol / 0 °C

With dmap; potassium fluoride; oxalyl dichloride; lithium diethylamide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 162584-15-8
(3S,4S)-3-[(2R,3S)-3-Benzyloxymethoxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyryl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-azetidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 73 percent / Et₃N, DMAP / CH₂Cl₂

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

3: 92 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 60 h / Ambient temperature

4: 94 percent / DIBAL-H / tetrahydrofuran; hexane / -25 °C

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

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

7: 96 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -78 °C

8: 85 percent / KF / methanol / 0 °C

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