(1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate

Base Information

Chemical Name:(1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate
CAS No.:872056-74-1
Molecular Formula:C₁₈H₁₈O₅
Molecular Weight:314.338
Hs Code.:

Synonyms:(1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate

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Chemical Property of (1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate

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Technology Process of (1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate

There total 3 articles about (1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate 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: 71.0%

: 872056-70-7
(1R,5S,6S)-6-ethyl 3-methyl 4-bromo-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate

: 100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6
styrene

: 872056-74-1
(1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate

Guidance literature:: With triethylamine; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 95 ℃; for 24h;
DOI:10.1021/ol051457m

Reference yield:

: 872056-69-4
(1R,3S,4R,5S,6S)-6-ethyl 3-methyl 3,4-dibromo-2-oxabicyclo[3.1.0]hexane-3,6-dicarboxylate

: 872056-74-1
(1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / DBU

2: 71 percent / NEt₃ / Pd(OAc)2; PPh₃ / dimethylformamide / 24 h / 95 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; 2: Heck coupling;
DOI:10.1021/ol051457m

Reference yield:

: 302349-65-1
(1S,5S,6S)-(-)-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylic acid 6-ethyl ester 3-methyl ester

: 872056-74-1
(1S,5R,6S)-6-ethyl 3-methyl 4-(E)-styryl-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / Br₂

2: 94 percent / DBU

3: 71 percent / NEt₃ / Pd(OAc)2; PPh₃ / dimethylformamide / 24 h / 95 °C

With bromine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; 3: Heck coupling;
DOI:10.1021/ol051457m