(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

Base Information

Chemical Name:(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene
CAS No.:741256-77-9
Molecular Formula:C₂₄H₃₀O₆
Molecular Weight:414.499
Hs Code.:

Synonyms:(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

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Chemical Property of (3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

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Technology Process of (3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

There total 4 articles about (3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene 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: 75.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 3-O-(4'-methoxybenzyl)-5-O-(2-methoxybenzyl)-5-C-vinyl-L-ido-pentafuranose

: 741256-77-9
(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In diethyl ether; at 20 ℃; for 1.5h;

3-O-(4'-methoxybenzyl)-5-O-(2-methoxybenzyl)-5-C-vinyl-L-ido-pentafuranose; In tetrahydrofuran; diethyl ether; at 20 ℃;
DOI:10.1248/cpb.52.727

Reference yield:

: 82529-87-1
(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 741256-77-9
(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

Guidance literature:: Multi-step reaction with 4 steps

1.1: copper iodide; dimethyl sulfide / tetrahydrofuran / 0.08 h / -40 °C

1.2: 75 percent / CH₂Cl₂ / 3 h / 20 °C

2.1: NaH / dimethylformamide / 2 h / ice bath cooling

2.2: 98 percent / dimethylformamide / 20 °C

3.1: 78 percent / aq. H₂SO₄ / tetrahydrofuran / 30 h / 60 °C

4.1: n-BuLi / diethyl ether / 1.5 h / 20 °C

4.2: 75 percent / diethyl ether; tetrahydrofuran / 20 °C

With copper(l) iodide; n-butyllithium; dimethylsulfide; sulfuric acid; sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1248/cpb.52.727

Reference yield:

: 741256-59-7
1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose

: 741256-77-9
(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 2 h / ice bath cooling

1.2: 98 percent / dimethylformamide / 20 °C

2.1: 78 percent / aq. H₂SO₄ / tetrahydrofuran / 30 h / 60 °C

3.1: n-BuLi / diethyl ether / 1.5 h / 20 °C

3.2: 75 percent / diethyl ether; tetrahydrofuran / 20 °C

With n-butyllithium; sulfuric acid; sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1248/cpb.52.727