(4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane

Base Information

Chemical Name:(4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane
CAS No.:863921-94-2
Molecular Formula:C₂₅H₃₇IO₄
Molecular Weight:528.471
Hs Code.:

Synonyms:(4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane

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Chemical Property of (4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane

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Technology Process of (4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane

There total 11 articles about (4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane 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: 92.0%

: 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

: 863921-94-2
(4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 0 ℃;
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

: 863921-94-2
(4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 4 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

4.1: 92 percent / iodine; triphenylphosphine; imidazole / benzene / 1 h / 0 °C

With 1H-imidazole; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; benzene;
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

: 863921-94-2
(4R,6R)-4-(2-Iodo-ethyl)-6-[(1E,3E)-(R)-8-(4-methoxy-benzyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 6 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

6.1: 92 percent / iodine; triphenylphosphine; imidazole / benzene / 1 h / 0 °C

With 1H-imidazole; disodium hydrogenphosphate; sodium amalgam; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1016/j.tet.2005.07.106