(2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

Base Information

Chemical Name:(2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde
CAS No.:853786-29-5
Molecular Formula:C₂₂H₂₆O₉
Molecular Weight:434.443
Hs Code.:

Synonyms:(2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

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Chemical Property of (2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

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Technology Process of (2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

There total 17 articles about (2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde 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: 85.0%

: 853786-28-4
(2S,3S)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

: 107-30-2
chloromethyl methyl ether

: 853786-29-5
(2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 18 ℃;
DOI:10.1016/j.tetasy.2005.02.035

Reference yield:

: 853786-20-6
ethyl (E)-3,5-dimethoxy-4-(methoxymethoxy)-cinnamate

: 853786-29-5
(2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / DIBAL-H / toluene; hexane / -10 °C

2: 78 percent / AD mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 0 °C

3: 73 percent / pyridine / 0 - 18 °C

4: 82 percent / K₂CO₃ / methanol / 3 h / 18 °C

5: 70 percent / DIAD; PPh₃ / toluene; tetrahydrofuran / 24 h / 18 °C

6: 70 percent / H₂ / Pd/C / ethyl acetate / 9 h / 18 °C

7: K₂CO₃ / methanol / 0.75 h / 18 °C

8: 85 percent / DIPEA; DMAP / CH₂Cl₂ / 0 - 18 °C

With pyridine; dmap; AD-mix-α; methanesulfonamide; di-isopropyl azodicarboxylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation / 5: Mitsunobu coupling;
DOI:10.1016/j.tetasy.2005.02.035

Reference yield:

: 4049-39-2
4-benzyloxy-3-hydroxy-benzaldehyde

: 853786-29-5
(2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / DIAD; PPh₃ / toluene; tetrahydrofuran / 24 h / 18 °C

2: 70 percent / H₂ / Pd/C / ethyl acetate / 9 h / 18 °C

3: K₂CO₃ / methanol / 0.75 h / 18 °C

4: 85 percent / DIPEA; DMAP / CH₂Cl₂ / 0 - 18 °C

With dmap; di-isopropyl azodicarboxylate; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; 1: Mitsunobu coupling;
DOI:10.1016/j.tetasy.2005.02.035