(1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester
CAS No.:844865-27-6
Molecular Formula:C₂₃H₂₃Br₂NO₆
Molecular Weight:569.247
Hs Code.:

Synonyms:(1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester

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Chemical Property of (1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester

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Technology Process of (1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester

There total 7 articles about (1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-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:

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

: 844865-27-6
(1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 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

With sodium azide; bromine; triethylamine; quinidine; In tetrahydrofuran; tetrachloromethane; dichloromethane; toluene; 5: Curtius rearrangement;
DOI:10.1021/jo048389m

Reference yield:

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

: 844865-27-6
(1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 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

With sodium azide; bromine; triethylamine; quinidine; In tetrahydrofuran; tetrachloromethane; dichloromethane; toluene; 5: Curtius rearrangement;
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

: 844865-27-6
(1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 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

With sodium azide; bromine; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 4: Curtius rearrangement;
DOI:10.1021/jo048389m