(2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid

Base Information

Chemical Name:(2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid
CAS No.:872056-88-7
Molecular Formula:C₁₅H₁₆O₅
Molecular Weight:276.289
Hs Code.:

Synonyms:(2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid

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Chemical Property of (2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid

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Technology Process of (2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid

There total 5 articles about (2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-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: 37.0%

: 872056-80-9
(1S,3R,4S,5S,6S)-6-ethyl 3-methyl 4-phenethyl-2-oxabicyclo[3.1.0]hexane-3,6-dicarboxylate

: (2R,3S,3aS,6aS)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid

: 872056-88-7
(2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 24h;
DOI:10.1021/ol051457m

Reference yield:

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

: 872056-88-7
(2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 71 percent / NEt₃ / Pd(OAc)2; PPh₃ / dimethylformamide / 24 h / 95 °C

2: 67 percent / H₂ / Pd/C / methanol / 48 h / 20 °C

3: hydrochloric acid / dioxane / 4 h / Heating

With hydrogenchloride; hydrogen; triethylamine; palladium diacetate; palladium on activated charcoal; triphenylphosphine; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; 1: Heck coupling;
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

: 872056-88-7
(2R,3S,3aR,6aR)-5-oxo-3-phenethylhexahydrofuro[2,3-b]furan-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / DBU

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

3: 67 percent / H₂ / Pd/C / methanol / 48 h / 20 °C

4: hydrochloric acid / dioxane / 4 h / Heating

With hydrogenchloride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium diacetate; palladium on activated charcoal; triphenylphosphine; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; 2: Heck coupling;
DOI:10.1021/ol051457m