(2S,2aS,2bS,5aS,6R)-2-Acetoxy-2b-methyl-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,2aS,2bS,5aS,6R)-2-Acetoxy-2b-methyl-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester
CAS No.:225219-91-0
Molecular Formula:C₁₉H₁₉NO₇
Molecular Weight:373.362
Hs Code.:

Synonyms:(2S,2aS,2bS,5aS,6R)-2-Acetoxy-2b-methyl-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-Acetoxy-2b-methyl-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-Acetoxy-2b-methyl-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

There total 10 articles about (2S,2aS,2bS,5aS,6R)-2-Acetoxy-2b-methyl-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: 85.0%

: 108-24-7
acetic anhydride

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

: 225219-91-0
(2S,2aS,2bS,5aS,6R)-2-Acetoxy-2b-methyl-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Guidance literature:: With pyridine; In dichloromethane; for 20h; Ambient temperature;
DOI:10.1016/S0040-4020(98)01152-1

Reference yield:

: 61550-05-8
trimethyl-(5-methyl-furan-2-yloxy)-silane

: 225219-91-0
(2S,2aS,2bS,5aS,6R)-2-Acetoxy-2b-methyl-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / ZnCl₂ / CH₂Cl₂; diethyl ether / 28 h / Ambient temperature

2: 1) NaHMDS / 1) THF, -78 deg C, 10 min, 2) THF, 6 h

3: 94 percent / LiHMDS / tetrahydrofuran / 12 h / Ambient temperature

4: 50 percent / TBAF, AcOH / tetrahydrofuran / 64 h

5: 77 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

6: 90 percent / DBU / benzene / 1.5 h / Ambient temperature

7: 1) O₃, 2) NaBH₃CN / 1) CH₂Cl₂, -78 deg C, 15 min, 2) CH₂Cl₂, 0 deg C, 10 min

8: 85 percent / pyridine / CH₂Cl₂ / 20 h / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium cyanoborohydride; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4020(98)01152-1

Reference yield:

: 159332-17-9
3S-<1R-(tert-butyldimethylsilanyloxy)ethyl>-4S-(2S-methyl-5-oxo-2,5-dihydrofuran-2-yl)azetidin-2-one

: 225219-91-0
(2S,2aS,2bS,5aS,6R)-2-Acetoxy-2b-methyl-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1) NaHMDS / 1) THF, -78 deg C, 10 min, 2) THF, 6 h

2: 94 percent / LiHMDS / tetrahydrofuran / 12 h / Ambient temperature

3: 50 percent / TBAF, AcOH / tetrahydrofuran / 64 h

4: 77 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

5: 90 percent / DBU / benzene / 1.5 h / Ambient temperature

6: 1) O₃, 2) NaBH₃CN / 1) CH₂Cl₂, -78 deg C, 15 min, 2) CH₂Cl₂, 0 deg C, 10 min

7: 85 percent / pyridine / CH₂Cl₂ / 20 h / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium cyanoborohydride; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1016/S0040-4020(98)01152-1