(5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

Base Information

Chemical Name:(5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate
CAS No.:1239015-25-8
Molecular Formula:C₁₇H₁₈O₅
Molecular Weight:302.327
Hs Code.:

Synonyms:(5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

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Chemical Property of (5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

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Technology Process of (5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

There total 7 articles about (5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-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: 80.0%

: 2-(5,6-dihydro-4H-pyran-2-carbonyl)-3-(4-methoxyphenyl)acrylic acid methyl ester

: 1239015-25-8
(5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

Guidance literature:: With 1,1,1,3',3',3'-hexafluoro-propanol; C₃₃H₂₉N₃O₃; sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; copper dichloride; In tert-butyl methyl ether; at 25 ℃; for 18h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1002/anie.200907266

Reference yield:

: 1007841-60-2
methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate

: 1239015-25-8
(5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

: methyl (5R,6S)-5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

Guidance literature:: methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate; With C₃₈H₃₈IrN₄S₂⁽¹⁺⁾*F₆P^(1-); In ethyl acetate; for 0.0166667h; Sonication; Sealed tube;

In ethyl acetate; at 40 ℃; for 14h; Solvent; stereoselective reaction; Sealed tube;
DOI:10.1002/adsc.201701546

Reference yield:

: 3,4-dihydro-2H-pyran-6-carbonyl chloride

: 1239015-25-8
(5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

: methyl (5R,6S)-5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 0.5 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere; Molecular sieve

3.1: piperidine; acetic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve; Schlenk technique

3.2: 16 h / 20 °C / Inert atmosphere; Schlenk technique

4.1: C₃₈H₃₈IrN₄S₂⁽¹⁺⁾*F₆P^(1-) / ethyl acetate / 0.02 h / Sonication; Sealed tube

4.2: 14 h / 40 °C / Sealed tube

With piperidine; C₃₈H₃₈IrN₄S₂⁽¹⁺⁾*F₆P^(1-); acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; ethyl acetate; 4.1: |Nazarov Cyclization / 4.2: |Nazarov Cyclization;
DOI:10.1002/adsc.201701546