(S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester

Base Information

Chemical Name:(S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester
CAS No.:105320-12-5
Molecular Formula:C₂₁H₃₃NO₄SeSi
Molecular Weight:470.543
Hs Code.:

Synonyms:(S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester

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Chemical Property of (S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester

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Technology Process of (S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester

There total 1 articles about (S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl 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:

: 5707-04-0
Phenylselenyl chloride

: 87037-96-5
(3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-(methoxycarbonyl)ethyl>azetidin-2-one

: 105320-12-5
(S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester

: 105371-00-4
(R)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester

Guidance literature:: With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, hexane, -45 deg C, 3.5 h, 2.) THF, hexane, -78 deg C, 20 min;
DOI:10.1021/jo00388a039

Reference yield: 69.0%

: 105320-12-5
(S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester

: 105320-13-6
(S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid

Guidance literature:: With sodium hydroxide; In methanol; water; at 60 ℃; for 2h;
DOI:10.1021/jo00388a039

Reference yield:

: 105320-12-5,105371-00-4
2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester

: 93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2
(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 96.1 percent / 30 percent H₂O₂ / CH₂Cl₂ / 0.5 h

2: 86 percent / DIBAL / toluene; tetrahydrofuran / 1 h / Ambient temperature

3: 89 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / Ambient temperature

4: H₂ / PtO₂ / ethyl acetate / 2.5 h / 2068.6 Torr / Ambient temperature

5: 439.1 mg / Jones reagent / diethyl ether

With jones reagent; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo00388a039