(4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one

Base Information

Chemical Name:(4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one
CAS No.:1360110-29-7
Molecular Formula:C₁₇H₁₉NO₅
Molecular Weight:317.342
Hs Code.:

Synonyms:(4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one

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Chemical Property of (4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one

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Technology Process of (4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one

There total 4 articles about (4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one 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: 79.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 1360110-27-5
diethyl [(4S,6R)-5,5-dimethyl-6-(4-nitrophenyl)-2-oxo-4-(2-oxopropyl)tetrahydro-2H-pyran-3-yl]phosphonate

: 1360110-29-7
(4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one

Guidance literature:: diethyl [(4S,6R)-5,5-dimethyl-6-(4-nitrophenyl)-2-oxo-4-(2-oxopropyl)tetrahydro-2H-pyran-3-yl]phosphonate; With potassium tert-butylate; In diethyl ether; at 20 ℃; for 0.5h;

formaldehyd; In diethyl ether; for 1h; optical yield given as %de;
DOI:10.1055/s-0031-1289629

Reference yield:

: 1360110-25-3
diethyl [(6R)-5,5-dimethyl-6-(4-nitrophenyl)-2-oxo-5,6-dihydro-2H-pyran-3-yl]phosphonate

: 1360110-29-7
(4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyrrolidine / 20 °C

2.1: potassium tert-butylate / diethyl ether / 0.5 h / 20 °C

2.2: 1 h

With pyrrolidine; potassium tert-butylate; In diethyl ether; 1.1: Michael addition / 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1289629

Reference yield:

: 1360110-23-1
(S)-2,2-dimethyl-1-(4-nitrophenyl)-3-oxopropyl (diethoxyphosphoryl)acetate

: 1360110-29-7
(4S,6R)-5,5-dimethyl-3-methylene-6-(4-nitrophenyl)-4-(2-oxopropyl)tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: piperidine; acetic acid / benzene / Reflux

2.1: pyrrolidine / 20 °C

3.1: potassium tert-butylate / diethyl ether / 0.5 h / 20 °C

3.2: 1 h

With pyrrolidine; piperidine; potassium tert-butylate; acetic acid; In diethyl ether; benzene; 1.1: Knoevenagel condensation / 2.1: Michael addition / 3.1: Horner-Wadsworth-Emmons olefination / 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1289629