(8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Base Information

Chemical Name:(8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid
CAS No.:714217-50-2
Molecular Formula:C₄₀H₆₀O₈
Molecular Weight:668.912
Hs Code.:

Synonyms:(8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

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Chemical Property of (8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

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Technology Process of (8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

There total 10 articles about (8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-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: 93.0%

: 565220-29-3
(8S,9R)-13-O-acetyl-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

: 714217-50-2
(8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Guidance literature:: With sodium hydroxide; In methanol; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2004.03.061

Reference yield:

: 64761-29-1
mesitaldehyde dimethylacetal

: 714217-50-2
(8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Guidance literature:: Multi-step reaction with 10 steps

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

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

3: 97 percent / sodium borohydride / propan-2-ol; ethyl acetate / 0.25 h / 20 °C

4: 188 mg / camphorsulfonic acid / CH₂Cl₂ / 5 h / 20 °C

5: 85 percent / LiAlH₄ / diethyl ether / 2 h / 30 °C

6: 74 percent / triethylamine; DMAP / CH₂Cl₂ / 32 h / 20 °C

7: 95 percent / triethylamine; DMAP / CH₂Cl₂ / 33 h / 20 °C

8: 99 percent / TBAF / tetrahydrofuran / 3.5 h / 20 °C

9: 80 percent / Jones reagent / acetone / 5 h / -30 °C

10: 93 percent / NaOH / methanol / 24 h / 20 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; isopropyl alcohol; acetone;
DOI:10.1016/j.tet.2004.03.061

Reference yield:

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

: 714217-50-2
(8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid

Guidance literature:: Multi-step reaction with 10 steps

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

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

3: 97 percent / sodium borohydride / propan-2-ol; ethyl acetate / 0.25 h / 20 °C

4: 188 mg / camphorsulfonic acid / CH₂Cl₂ / 5 h / 20 °C

5: 85 percent / LiAlH₄ / diethyl ether / 2 h / 30 °C

6: 74 percent / triethylamine; DMAP / CH₂Cl₂ / 32 h / 20 °C

7: 95 percent / triethylamine; DMAP / CH₂Cl₂ / 33 h / 20 °C

8: 99 percent / TBAF / tetrahydrofuran / 3.5 h / 20 °C

9: 80 percent / Jones reagent / acetone / 5 h / -30 °C

10: 93 percent / NaOH / methanol / 24 h / 20 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; isopropyl alcohol; acetone;
DOI:10.1016/j.tet.2004.03.061