(3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate

Base Information

• Chemical Name: (3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate
• CAS No.: 1111644-82-6
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37

Synonyms:(3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate

Chemical Property of (3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate

There total 3 articles about (3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate 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: 70.0%

trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate (1111644-44-0) + 3-phenyl-propenal (104-55-2) → (3aR,4S,5S,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate (1111644-81-5) + (3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate (1111644-82-6) + (3aS,4R,5S,6aS)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate (1111644-49-5)

Guidance literature:

trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate; 3-phenyl-propenal; With (5aS,10bR)-2-mesityl-3-methyl-4,5a,6,10b-tetrahydroimidazo[1,5-d]indeno[2,1-b][1,4]oxazin-2-ium perchlorate; In toluene; at 20 ℃; for 0.0833333h; Inert atmosphere;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃; for 18h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ol802739d

Reference yield: 65.0%

trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate (1111644-44-0) + 3-phenyl-propenal (104-55-2) → (1S,2R,3R,5R)-ethyl-5-(2-hydroxypropan-2-yl)-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3-carboxylate (1111644-47-3) + (1S,2S,3R,5R)-ethyl-5-(2-hydroxypropan-2-yl)-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3-carboxylate (1111644-50-8) + (3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate (1111644-82-6) + (3aS,4R,5S,6aS)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate (1111644-49-5)

Guidance literature:

trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate; 3-phenyl-propenal; With (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; In toluene; at -10 ℃; for 0.25h; Inert atmosphere;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at -10 - 20 ℃; for 16h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ol802739d

Reference yield:

trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate (1111644-44-0) + 3-phenyl-propenal (104-55-2) → (3aR,4S,5R,6aR)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate (1111644-82-6) + (3aS,4R,5S,6aS)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate (1111644-49-5) + (3aS,4R,5R,6aS)-ethyl-6a-hydroxy-1,1-dimethyl-3-oxo-4-phenylhexahydro-1H-cyclopenta[c]furan-5-carboxylate (1111644-76-8)

Guidance literature:

trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate; 3-phenyl-propenal; With C₂₃H₂₅N₂O⁽¹⁺⁾*ClO₄^(1-); In toluene; at 20 ℃; for 0.0833333h; Inert atmosphere;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃; for 18h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ol802739d

upstream raw materials:

trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate

3-phenyl-propenal

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