2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol

Base Information

Chemical Name:2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol
CAS No.:863921-93-1
Molecular Formula:C₂₅H₃₈O₅
Molecular Weight:418.574
Hs Code.:

Synonyms:2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol

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Chemical Property of 2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol

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Technology Process of 2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol

There total 10 articles about 2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol 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: 89.0%

: 863921-92-0
tert-Butyl-(2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethoxy)-diphenyl-silane

: 863921-93-1
2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1246/cl.2005.906

Reference yield:

: 863921-90-8
{2-[(4S,6R)-6-((1E,3E)-5-Bromo-penta-1,3-dienyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-diphenyl-silane

: 863921-93-1
2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 93 percent / tetrahydrofuran; hexane / -78 - -40 °C

2.1: 66 percent / Na₂HPO₄; Na/Hg / methanol / 5 h / 0 - 20 °C

3.1: 89 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; hexane;
DOI:10.1016/j.tet.2005.07.106

Reference yield:

: (2E,4E)-5-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-penta-2,4-dienoic acid ethyl ester

: 863921-93-1
2-{(4S,6R)-6-[(1E,3E)-(R)-8-(4-Methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

2.1: 95 percent / triphenylphosphane; NBS / CH₂Cl₂ / 0.5 h / -78 °C

3.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 93 percent / tetrahydrofuran; hexane / -78 - -40 °C

4.1: 66 percent / Na₂HPO₄; Na/Hg / methanol / 5 h / 0 - 20 °C

5.1: 89 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With disodium hydrogenphosphate; sodium amalgam; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1016/j.tet.2005.07.106