(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

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Chemical Name:(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
CAS No.:225219-84-1
Molecular Formula:C₁₈H₁₉NO₆
Molecular Weight:345.352
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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: 58.0%

: 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

: 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:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 48h; Ambient temperature;
DOI:10.1016/S0040-4020(98)01152-1

Reference yield:

: 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

: 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 5 steps

1: 80 percent / ZnCl₂ / CH₂Cl₂; diethyl ether / 20 h / Ambient temperature

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

3: 81 percent / LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4: 71 percent / Bu₃SnH, AIBN / toluene / 2 h / 90 °C

5: 58 percent / TBAF, AcOH / tetrahydrofuran / 48 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; acetic acid; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; 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

: 225219-84-1
(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