(9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Base Information

Chemical Name:(9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide seco-acid
CAS No.:714217-41-1
Molecular Formula:C₄₀H₅₈O₇
Molecular Weight:650.896
Hs Code.:

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

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Chemical Property of (9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Chemical Property:

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Technology Process of (9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

There total 6 articles about (9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide 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:

: 64761-29-1
mesitaldehyde dimethylacetal

: 714217-41-1
(9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Guidance literature:: Multi-step reaction with 6 steps

1: 57 percent / camphorsulfonic acid / CH₂Cl₂ / 6 h / 20 °C

2: 118 mg / aq. NaHCO₃ / tetrahydrofuran / 0.33 h / 0 °C

3: 64 percent / CrCl₂ / acetone; H₂O / 3 h / 0 °C

4: 91 percent / CeCl₃*H₂O; NaBH₄ / tetrahydrofuran / 4.5 h / -25 °C

5: 86 percent / camphorsulfonic acid / 24 h / 20 °C

6: 86 percent / NaOH / dimethylsulfoxide / 5 h / 90 °C

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

Reference yield:

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

: 714217-41-1
(9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Guidance literature:: Multi-step reaction with 6 steps

1: 57 percent / camphorsulfonic acid / CH₂Cl₂ / 6 h / 20 °C

2: 118 mg / aq. NaHCO₃ / tetrahydrofuran / 0.33 h / 0 °C

3: 64 percent / CrCl₂ / acetone; H₂O / 3 h / 0 °C

4: 91 percent / CeCl₃*H₂O; NaBH₄ / tetrahydrofuran / 4.5 h / -25 °C

5: 86 percent / camphorsulfonic acid / 24 h / 20 °C

6: 86 percent / NaOH / dimethylsulfoxide / 5 h / 90 °C

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

Reference yield:

: 714217-53-5
(1S,2R,5R,6R,7S,8R,10S,12S,13S,15S,17R)-7,10-Dihydroxy-10-iodomethyl-2,5,6,8,12,17-hexamethyl-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione

: 714217-41-1
(9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Guidance literature:: Multi-step reaction with 5 steps

1: 118 mg / aq. NaHCO₃ / tetrahydrofuran / 0.33 h / 0 °C

2: 64 percent / CrCl₂ / acetone; H₂O / 3 h / 0 °C

3: 91 percent / CeCl₃*H₂O; NaBH₄ / tetrahydrofuran / 4.5 h / -25 °C

4: 86 percent / camphorsulfonic acid / 24 h / 20 °C

5: 86 percent / NaOH / dimethylsulfoxide / 5 h / 90 °C

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