(E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester

Base Information

Chemical Name:(E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester
CAS No.:107668-57-5
Molecular Formula:C₂₇H₄₂N₂O₉S₂Si
Molecular Weight:630.856
Hs Code.:

(E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester

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Chemical Property of (E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester

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Technology Process of (E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester

There total 4 articles about (E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester 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: 90.0%

: (Z)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-hydroxy-but-2-enoic acid 4-nitro-benzyl ester

: 124-63-0
methanesulfonyl chloride

: 107668-57-5,107741-69-5
(E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester

Guidance literature:: With triethylamine; In dichloromethane; at -20 ℃;
DOI:10.1016/S0040-4039(00)84711-5

Reference yield:

: 94944-10-2
(3R,4R)-4-benzoyloxy-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one

: 107668-57-5,107741-69-5
(E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / NaH / dimethylformamide

2: 83 percent / Cs₂CO₃ / acetonitrile / overnight

3: 75 percent / LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

4: 90 percent / NEt₃ / CH₂Cl₂ / -20 °C

With sodium hydride; caesium carbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)84711-5

Reference yield:

: 107668-54-2
(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-butylsulfanyl-azetidin-2-one

: 107668-57-5,107741-69-5
(E)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / Cs₂CO₃ / acetonitrile / overnight

2: 75 percent / LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

3: 90 percent / NEt₃ / CH₂Cl₂ / -20 °C

With caesium carbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)84711-5