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

Base Information

Chemical Name:(9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide seco-acid
CAS No.:565220-25-9
Molecular Formula:C₃₃H₅₂O₇
Molecular Weight:560.772
Hs Code.:

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

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

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

There total 4 articles about (9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide seco-acid 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: 97.0%

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

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

Guidance literature:: With sodium hydroxide; In dimethyl sulfoxide; at 90 ℃; for 12h;
DOI:10.1016/j.tet.2004.03.061

Reference yield:

: 116417-70-0
(8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide

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

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / PPTS / CH₂Cl₂ / 1 h / 20 °C

2: 355 mg / aq. NaHCO₃ / tetrahydrofuran / 0.67 h / 0 °C

3: 82 percent / CrCl₂ / acetone; H₂O / 0.5 h / 0 °C

4: 205 mg / CeCl₃*7H₂O; NaBH₄ / tetrahydrofuran / 4.5 h / -25 °C

5: 66 percent / camphorsulfonic acid / CH₂Cl₂ / 6 h / 20 °C

6: 97 percent / NaOH / dimethylsulfoxide / 12 h / 90 °C

With chromium dichloride; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1016/j.tet.2004.03.061

Reference yield:

: 160691-43-0
(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

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

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / camphorsulfonic acid / CH₂Cl₂ / 6 h / 20 °C

2: 97 percent / NaOH / dimethylsulfoxide / 12 h / 90 °C

With sodium hydroxide; camphor-10-sulfonic acid; In dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tet.2004.03.061