(3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate

Base Information

Chemical Name:(3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate
CAS No.:1042450-60-1
Molecular Formula:C₁₆H₁₈O₄
Molecular Weight:274.317
Hs Code.:

Synonyms:(3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate

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Chemical Property of (3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate

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Technology Process of (3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate

There total 3 articles about (3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-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: 65.0%

: 6742-53-6,10150-93-3,200628-30-4
(E)-ethyl 4-oxo-2-pentenoate

: 1262801-38-6
1-oxo-3-phenylpropan-2-yl p-nitrobenzoate

: 1042450-60-1
(3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate

Guidance literature:: 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; caesium carbonate; In tetrahydrofuran; at 40 ℃; for 7h; stereoselective reaction; Inert atmosphere; Sealed tube;
DOI:10.1016/j.tetasy.2017.01.002

Reference yield: 65.0%

: 6742-53-6,10150-93-3,200628-30-4
(E)-ethyl 4-oxo-2-pentenoate

: sodium 2-chloro-1-hydroxy-3-phenylpropane-1-sulfonate

: 1042450-60-1
(3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate

Guidance literature:: sodium 2-chloro-1-hydroxy-3-phenylpropane-1-sulfonate; With potassium carbonate; In water; toluene; for 0.0833333h;

(E)-ethyl 4-oxo-2-pentenoate; With C₁₃H₁₄N₃O₃S⁽¹⁺⁾*Cl^(1-); In water; toluene; at 20 ℃; for 6h; optical yield given as %ee; enantioselective reaction;
DOI:10.1021/ol801502h

Reference yield:

: 87-91-2
diethyl (2R,3R)-tartrate

: 1042450-60-1
(3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: periodic acid / diethyl ether / 3 h / 20 - 25 °C

1.2: 16 h / 0 - 25 °C

2.1: (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; caesium carbonate / tetrahydrofuran / 7 h / 40 °C / Inert atmosphere; Sealed tube

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; caesium carbonate; periodic acid; In tetrahydrofuran; diethyl ether; 2.1: |Diels-Alder Cycloaddition;
DOI:10.1016/j.tetasy.2017.01.002