3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)azetidin-2-one

Base Information

Chemical Name:3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)azetidin-2-one
CAS No.:225219-80-7
Molecular Formula:C₂₁H₂₉NO₄SSi
Molecular Weight:419.617
Hs Code.:

Synonyms:3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)azetidin-2-one

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Chemical Property of 3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)azetidin-2-one

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Technology Process of 3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)azetidin-2-one

There total 1 articles about 3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)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: 80.0%

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: trimethyl-(5-phenylsulfanyl-furan-2-yloxy)-silane

: 225219-80-7
3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)azetidin-2-one

Guidance literature:: With zinc(II) chloride; In diethyl ether; dichloromethane; for 20h; Ambient temperature;
DOI:10.1016/S0040-4020(98)01152-1

Reference yield:

: 225219-80-7
3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)azetidin-2-one

: 225219-84-1
(2S,2aS,2bS,5aS,6R)-2-((R)-1-Hydroxy-ethyl)-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1) LiHMDS / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 5 h; room temperature, 1 h

2: 81 percent / LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

3: 71 percent / Bu₃SnH, AIBN / toluene / 2 h / 90 °C

4: 58 percent / TBAF, AcOH / tetrahydrofuran / 48 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1016/S0040-4020(98)01152-1

Reference yield:

: 225219-80-7
3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(5-oxo-2R-phenylsulfanyl-2,5-dihydrofuran-2-yl)azetidin-2-one

: 225219-83-0
(2S,2aS,2bS,5aS,6R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1) LiHMDS / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 5 h; room temperature, 1 h

2: 81 percent / LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

3: 71 percent / Bu₃SnH, AIBN / toluene / 2 h / 90 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1016/S0040-4020(98)01152-1