6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid

Base Information

Chemical Name:6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid
CAS No.:158177-68-5
Molecular Formula:C₂₀H₁₇NO₅
Molecular Weight:351.359
Hs Code.:

Synonyms:6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid

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Chemical Property of 6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid

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Technology Process of 6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid

There total 10 articles about 6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid 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: 100.0%

: 158177-62-9
(2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine

: 158177-68-5
6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid

Guidance literature:: With trifluoroacetic acid; at 0 - 20 ℃; for 12h;
DOI:10.1016/S0040-4020(97)00191-9

Reference yield:

: 98-88-4
benzoyl chloride

: 158177-68-5
6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / 1 N NaOH / diethyl ether

2: 82 percent / benzene; various solvent(s) / Heating

3: 97 percent / NaIO₄, RuO₂*H₂O / H₂O; CCl₄; CHCl₃

4: molsieves 5 A / benzene

5: 1.) K₂CO₃ / 1.) CH₃CN; 2.) H₂O, CH₃CO₂H

6: CeCl₃ / tetrahydrofuran; diethyl ether

7: trifluoroacetic acid

With ruthenium(IV) oxide; sodium hydroxide; sodium periodate; cerium(III) chloride; 5A molecular sieve; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; diethyl ether; chloroform; water; benzene;
DOI:10.1016/0040-4039(94)88105-7

Reference yield:

: 31560-19-7
(2S,4R)-1-benzoyl-4-hydroxy-L-proline

: 158177-68-5
6-benzoyl-2-oxo-8(S)-phenyl-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / benzene; various solvent(s) / Heating

2: 97 percent / NaIO₄, RuO₂*H₂O / H₂O; CCl₄; CHCl₃

3: molsieves 5 A / benzene

4: 1.) K₂CO₃ / 1.) CH₃CN; 2.) H₂O, CH₃CO₂H

5: CeCl₃ / tetrahydrofuran; diethyl ether

6: trifluoroacetic acid

With ruthenium(IV) oxide; sodium periodate; cerium(III) chloride; 5A molecular sieve; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; diethyl ether; chloroform; water; benzene;
DOI:10.1016/0040-4039(94)88105-7