1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate

Base Information

Chemical Name:1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate
CAS No.:158466-53-6
Molecular Formula:C₁₈H₂₄O₇
Molecular Weight:352.384
Hs Code.:

Synonyms:1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate

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Chemical Property of 1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate

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Technology Process of 1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate

There total 2 articles about 1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate 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:

: 158466-52-5
1,1-Dimethylethyl (αS,2R,4R)-α-hydroxy-2-(3,4-dimethoxyphenyl)-1,3-dioxane-4-acetate

: 158466-53-6
1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 25 ℃; for 2h; Yield given;
DOI:10.1021/jo00121a026

Reference yield:

: 1,1-Dimethylethyl 2,3-dihydroxy-5-<(3,4-dimethoxyphenyl)methoxy>pentanoate

: 158466-53-6
1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / DDQ, pyridine, molecular sieves 4 Angstroem / CH₂Cl₂ / 24 h / 5 °C

2: pyridine, Dess-Martin periodinane / CH₂Cl₂ / 2 h / 25 °C

With pyridine; 4 A molecular sieve; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1021/jo00121a026

Reference yield:

: 158466-53-6
1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate

: 158466-61-6
(2R,3R)-2-Methoxy-4-methyl-1-(phenylthio)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

Guidance literature:: Multi-step reaction with 8 steps

1: t-BuOK / tetrahydrofuran / 1.) r.t., 40 min, 2.) -60 to -40 deg C, 1 h; -42 to -20 deg C, 3 h

2: 98 percent / PPTS / methanol / 3.5 h / 25 °C

3: 89 percent / imidazole / CH₂Cl₂ / 18 h / 25 °C

4: 95 percent / aq. AcOH / tetrahydrofuran / 4 h / 25 °C

5: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.42 h / 25 °C

6: 91 percent / 2-methyl-2-butene, aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 0.67 h / 25 °C

7: Et₃N / toluene / 2 h / 25 °C

8: DMAP / toluene / 3 h / 60 °C

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium tert-butylate; pyridinium p-toluenesulfonate; Dess-Martin periodane; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo00121a026