(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

Base Information

Chemical Name:(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol
CAS No.:1448328-55-9
Molecular Formula:C₃₀H₄₂O₆
Molecular Weight:498.66
Hs Code.:

Synonyms:(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

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Chemical Property of (2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

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Technology Process of (2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

There total 10 articles about (2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-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: 94.0%

: 1448328-54-8
(2R,3S,5Z,7S,10E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-dien-7-ol

: 1448328-55-9
(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 3h;
DOI:10.1002/anie.201208919

Reference yield:

: 1448328-52-6
(2R,3S,7S,E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)tetradec-10-en-5-yn-7-ol

: 1448328-55-9
(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

Guidance literature:: Multi-step reaction with 2 steps

1.1: iron(III)-acetylacetonate; 1,2-bis-(diphenylphosphino)ethane / tetrahydrofuran / 0.17 h / -78 °C

1.2: 20 h / -78 - 0 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

With iron(III)-acetylacetonate; tetrabutyl ammonium fluoride; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran;
DOI:10.1002/anie.201208919

Reference yield:

: 198411-03-9
(E)-8-(benzyloxy)oct-4-en-1-ol

: 1448328-55-9
(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

Guidance literature:: Multi-step reaction with 4 steps

1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

2.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / toluene / 1.5 h / 20 °C / Inert atmosphere

2.2: 21 h / 20 °C / Inert atmosphere

3.1: iron(III)-acetylacetonate; 1,2-bis-(diphenylphosphino)ethane / tetrahydrofuran / 0.17 h / -78 °C

3.2: 20 h / -78 - 0 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

With iron(III)-acetylacetonate; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; zinc trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/anie.201208919