(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

Base Information

Chemical Name:(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine
CAS No.:853786-30-8
Molecular Formula:C₃₃H₄₀O₁₂
Molecular Weight:628.673
Hs Code.:

(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

Synonyms:(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

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Chemical Property of (2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

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Technology Process of (2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

There total 22 articles about (2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine 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: 41.0%

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

: 3,5-bis-(methoxymethoxy)benzyltriphenylphosphonium chloride

: 853786-30-8
(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

Guidance literature:: With cesium fluoride; In toluene; for 6h; Heating;
DOI:10.1016/j.tetasy.2005.02.035

Reference yield:

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

: 853786-30-8
(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

Guidance literature:: Multi-step reaction with 9 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

9: 41 percent / CsF / toluene / 6 h / Heating

With pyridine; dmap; AD-mix-α; methanesulfonamide; di-isopropyl azodicarboxylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; cesium fluoride; 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

: 853786-30-8
(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

Guidance literature:: Multi-step reaction with 5 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

5: 41 percent / CsF / toluene / 6 h / Heating

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