(1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
CAS No.:844865-34-5
Molecular Formula:C₃₁H₃₂N₂O₅
Molecular Weight:512.605
Hs Code.:

Synonyms:(1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

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Chemical Property of (1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

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Technology Process of (1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

There total 10 articles about (1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic 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:

: 6118-51-0
exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

: 844865-34-5
(1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: quinidine / CCl₄; toluene / -55 °C

2: Et₃N / tetrahydrofuran / -30 - -10 °C

3: aq. NaN₃ / tetrahydrofuran / -10 - 20 °C

4: Br₂ / CH₂Cl₂ / 0 - 20 °C

5: toluene / 0.5 h / Heating

6: toluene / Heating

7: Zn; TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 0 °C

8: NaH / dimethylformamide / 0 - 20 °C

9: TFA / CH₂Cl₂ / 1 h / 20 °C

10: aq. NaOH / dioxane / 1 h / 20 °C

11: 20 °C

With sodium hydroxide; sodium azide; bromine; titanium tetrachloride; sodium hydride; triethylamine; trifluoroacetic acid; zinc; quinidine; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Curtius rearrangement / 11: Ugi reaction;
DOI:10.1021/jo048389m

Reference yield:

: 648433-21-0
(2R,3S)-3-exo-benzyloxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid

: 844865-34-5
(1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N / tetrahydrofuran / -30 - -10 °C

2: aq. NaN₃ / tetrahydrofuran / -10 - 20 °C

3: Br₂ / CH₂Cl₂ / 0 - 20 °C

4: toluene / 0.5 h / Heating

5: toluene / Heating

6: Zn; TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 0 °C

7: NaH / dimethylformamide / 0 - 20 °C

8: TFA / CH₂Cl₂ / 1 h / 20 °C

9: aq. NaOH / dioxane / 1 h / 20 °C

10: 20 °C

With sodium hydroxide; sodium azide; bromine; titanium tetrachloride; sodium hydride; triethylamine; trifluoroacetic acid; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Curtius rearrangement / 10: Ugi reaction;
DOI:10.1021/jo048389m

Reference yield:

: 844865-25-4
(1R,2S,3R,4S)-3-Azidocarbonyl-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester

: 844865-34-5
(1R,2R,3R,4S)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Br₂ / CH₂Cl₂ / 0 - 20 °C

2: toluene / 0.5 h / Heating

3: toluene / Heating

4: Zn; TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 0 °C

5: NaH / dimethylformamide / 0 - 20 °C

6: TFA / CH₂Cl₂ / 1 h / 20 °C

7: aq. NaOH / dioxane / 1 h / 20 °C

8: 20 °C

With sodium hydroxide; bromine; titanium tetrachloride; sodium hydride; trifluoroacetic acid; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Curtius rearrangement / 8: Ugi reaction;
DOI:10.1021/jo048389m