(3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

Base Information

Chemical Name:(3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one
CAS No.:954114-86-4
Molecular Formula:C₂₀H₂₂O₄
Molecular Weight:326.392
Hs Code.:

Synonyms:(3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

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Chemical Property of (3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

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Technology Process of (3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

There total 15 articles about (3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-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: 92.0%

: 954114-85-3
(4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-4-methyldihydrofuran-2(3H)-one

: 74-88-4
methyl iodide

: 954114-86-4
(3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

Guidance literature:: (4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-4-methyldihydrofuran-2(3H)-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/ol7016388

Reference yield: 69.0%

: (3S,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

: 954114-86-4
(3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 16h;
DOI:10.1021/acs.joc.5b00945

Reference yield:

: 954114-83-1
(2R,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-methylpropan-1-ol

: 954114-86-4
(3R,4R,5S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 948.7 mg / dimethylsulfoxide / 2 h / 70 °C

3.1: NaOH / tetrahydrofuran; methanol; H₂O / 12 h / 140 °C

3.2: 70 percent / HCl / various solvents / 12 h / 20 °C

4.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 92 percent / tetrahydrofuran / 1 h / -78 °C

With sodium hydroxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/ol7016388