(1S,2R,5R)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-dicarboxylate

Base Information

Chemical Name:(1S,2R,5R)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-dicarboxylate
CAS No.:1491156-33-2
Molecular Formula:C₁₇H₁₈O₆
Molecular Weight:318.326
Hs Code.:

Synonyms:(1S,2R,5R)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-dicarboxylate

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Chemical Property of (1S,2R,5R)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-dicarboxylate

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Technology Process of (1S,2R,5R)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-dicarboxylate

There total 2 articles about (1S,2R,5R)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-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: 88.0%

: 14371-10-9
(E)-3-phenylpropenal

: 24889-15-4
methyl 2-(methoxycarbonyl)-4-oxopentanonate

: 1491156-33-2
(1S,2R,5R)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-dicarboxylate

: (1R,2S,5S)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-dicarboxylate

Guidance literature:: methyl 2-(methoxycarbonyl)-4-oxopentanonate; With (5aS,10bR)-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; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In toluene; at 20 ℃; for 0.0833333h; Schlenk technique; Inert atmosphere;

(E)-3-phenylpropenal; In toluene; at 20 ℃; for 1h; Reagent/catalyst; Solvent; Temperature; enantioselective reaction; Catalytic behavior; Schlenk technique; Inert atmosphere;
DOI:10.1002/anie.201405200

Reference yield: 80.0%

: 24889-15-4
methyl 2-(methoxycarbonyl)-4-oxopentanonate

: 102-92-1,17082-09-6
cinnamoyl chloride

: 1491156-33-2
(1S,2R,5R)-dimethyl 5-methyl-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3,3-dicarboxylate

Guidance literature:: methyl 2-(methoxycarbonyl)-4-oxopentanonate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 0.166667h;

With 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.166667h;

cinnamoyl chloride; at 0 - 23 ℃; enantioselective reaction;
DOI:10.1038/nchem.1788