(2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Base Information

Chemical Name:(2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
CAS No.:1446094-78-5
Molecular Formula:C₂₄H₂₅BrO₄
Molecular Weight:457.364
Hs Code.:

Synonyms:(2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

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Chemical Property of (2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

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Technology Process of (2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

There total 2 articles about (2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-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:

: 55177-35-0
(E)-4-phenyl-2-butenal

: 1379601-12-3
(E)-tert-butyl 4-(4-bromophenyl)-2-oxobut-3-enoate

: 1446094-78-5
(2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

: tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Guidance literature:: With diethylacetamide; (S)-2-(((2-((3,5-bis(trifluoromethyl)phenyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)methyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate; In tetrahydrofuran; at 20 ℃; for 42h; Overall yield = 74 %; stereoselective reaction;
DOI:10.1002/anie.201207122

Reference yield:

: potassium (E)-4-(4-bromophenyl)-2-oxobut-3-enoate

: 1446094-78-5
(2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

: tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogenchloride / dichloromethane; water

1.2: 20 °C / Inert atmosphere

2.1: (S)-2-(((2-((3,5-bis(trifluoromethyl)phenyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)methyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate; diethylacetamide / tetrahydrofuran / 42 h / 20 °C

With hydrogenchloride; diethylacetamide; (S)-2-(((2-((3,5-bis(trifluoromethyl)phenyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)methyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate; In tetrahydrofuran; dichloromethane; water; 2.1: |Diels-Alder Cycloaddition;
DOI:10.1002/anie.201207122

Reference yield: 45.0%

: 19693-75-5
2-methoxy-1,3-dioxolane

: 1446094-78-5
(2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

: 1446095-07-3
(2R,3R,4R,5R,6R)-tert-butyl 6-((1,3-dioxolan-2-yl)methyl)-4-(4-bromophenyl)-2,3-dihydroxy-5-phenyltetrahydro-2H-pyran-2-carboxylate

Guidance literature:: 2-methoxy-1,3-dioxolane; (2R,3R,4S)-tert-butyl 4-(4-bromophenyl)-2-(2-oxoethyl)-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate; With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 3h;

With potassium osmate; methanesulfonamide; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; for 24h; diastereoselective reaction;
DOI:10.1002/anie.201207122