7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[(phenylmethyl)amino]-, phenylmethyl ester, (1R,2R,3R,4S)-

Base Information

Chemical Name:7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[(phenylmethyl)amino]-, phenylmethyl ester, (1R,2R,3R,4S)-
CAS No.:844865-51-6
Molecular Formula:C21H21NO3
Molecular Weight:335.403
Hs Code.:

Synonyms:

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Chemical Property of 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[(phenylmethyl)amino]-, phenylmethyl ester, (1R,2R,3R,4S)-

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Technology Process of 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[(phenylmethyl)amino]-, phenylmethyl ester, (1R,2R,3R,4S)-

There total 10 articles about 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[(phenylmethyl)amino]-, phenylmethyl ester, (1R,2R,3R,4S)- 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

: 844865-51-6
(1R,2R,3R,4S)-3-Benzylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 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

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

Reference yield:

: 844865-29-8
(1R,2R,3R,4S)-3-[Benzyl-(4-methoxy-benzyloxycarbonyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester

: 844865-51-6
(1R,2R,3R,4S)-3-Benzylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/jo048389m

Reference yield:

: 100-51-6,185532-71-2
benzyl alcohol

: 844865-51-6
(1R,2R,3R,4S)-3-Benzylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 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

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