3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide

Base Information

• Chemical Name: 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide
• CAS No.: 565220-26-0
• Molecular Formula: C₃₃H₅₀O₆
• Molecular Weight: 542.756

Synonyms:3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide

Chemical Property of 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide

Chemical Property:

Purity/Quality:

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Technology Process of 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide

There total 5 articles about 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide 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: 96.0%

(9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide seco-acid (565220-25-9) → 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide (565220-26-0)

Guidance literature:

(9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide seco-acid; With 2,4,6-trichlorobenzoyl chloride; In toluene;

With dmap; In toluene; at 130 ℃; for 11h;

DOI:10.1016/S0040-4039(03)00954-7

Reference yield: 66.0%

mesitaldehyde dimethylacetal (64761-29-1) + (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-9,11-dihydroxy-3,5-(isopropylidenedioxy)-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide (160691-43-0) → 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide (565220-26-0)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2004.03.061

Reference yield:

C40H53Cl3O8 → 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide (565220-26-0)

Guidance literature:

With dmap; In tetrahydrofuran; toluene; at 130 ℃; for 11h;

DOI:10.1016/j.tet.2004.03.061

upstream raw materials:

mesitaldehyde dimethylacetal

(2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-9,11-dihydroxy-3,5-(isopropylidenedioxy)-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide

(9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide seco-acid

(8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide

Downstream raw materials:

(9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide seco-acid

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