(2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol

Base Information

Chemical Name:(2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol
CAS No.:714217-47-7
Molecular Formula:C₄₀H₆₂O₇
Molecular Weight:654.928
Hs Code.:

Synonyms:(2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol

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Chemical Property of (2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol

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Technology Process of (2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol

There total 5 articles about (2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol 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: 85.0%

: 565220-27-1
(9R)-9-dihydro-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-oleandonolide

: 714217-47-7
(2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 30 ℃; for 2h;
DOI:10.1016/j.tet.2004.03.061

Reference yield:

: 64761-29-1
mesitaldehyde dimethylacetal

: 714217-47-7
(2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol

Guidance literature:: Multi-step reaction with 5 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

With sodium tetrahydroborate; lithium aluminium tetrahydride; camphor-10-sulfonic acid; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; isopropyl alcohol;
DOI:10.1016/j.tet.2004.03.061

Reference yield:

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

: 714217-47-7
(2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol

Guidance literature:: Multi-step reaction with 5 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

With sodium tetrahydroborate; lithium aluminium tetrahydride; camphor-10-sulfonic acid; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; isopropyl alcohol;
DOI:10.1016/j.tet.2004.03.061