(4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

Base Information

Chemical Name:(4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde
CAS No.:104777-87-9
Molecular Formula:C₁₉H₂₃NO₈
Molecular Weight:393.394
Hs Code.:

Synonyms:(4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

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Chemical Property of (4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

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Technology Process of (4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

There total 12 articles about (4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-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: 65.0%

: 104777-86-8
4-[(4R,5S,6S)-5-(3,4-Dimethoxy-benzyloxy)-6-hydroxymethyl-[1,3]dioxan-4-yl]-piperidine-2,6-dione

: 104777-87-9
(4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

Guidance literature:: With pyridine; chromium(VI) oxide; In acetic anhydride; Ambient temperature;
DOI:10.1039/c39860000396

Reference yield:

: 113473-80-6
4-((4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

: 104777-87-9
(4S,5R,6S)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / Pd/C / methanol / 4 h

2: p. TsOH monohydrate / toluene / 5 h / Heating; azeotropic removal of water

3: diethylaluminium chloride, triethylsilane / toluene; CH₂Cl₂ / 1.5 h / -60 - -55 °C

4: CrO₃, pyridine, acetic anhydride / CH₂Cl₂; dimethylformamide / 0.13 h / Ambient temperature

With pyridine; chromium(VI) oxide; triethylsilane; hydrogen; diethylaluminium chloride; acetic anhydride; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)81662-8

Reference yield:

: 102487-45-6,102518-68-3,112419-11-1
4-((4R,5S,6S)-5-Hydroxy-6-hydroxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

: 104777-87-9
(4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent

2: 61 percent / Et₂AlCl, Et₃SiH / CH₂Cl₂ / -55 °C

3: 65 percent / CrO₃, pyridine / acetic anhydride / Ambient temperature

With pyridine; chromium(VI) oxide; triethylsilane; diethylaluminium chloride; In dichloromethane; acetic anhydride;
DOI:10.1039/c39860000396