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

Base Information

• Chemical Name: (3S,4R,5R,6S)-3,5-di-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene
• CAS No.: 741256-62-2
• Molecular Formula: C₂₄H₃₀O₆
• Molecular Weight: 414.499
• Mol file: 741256-62-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (3S,4R,5R,6S)-3,5-di-(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: 70.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 3,5-O-di(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose → (3S,4R,5R,6S)-3,5-di-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene (741256-62-2)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In diethyl ether; at 20 ℃; for 2h;

3,5-O-di(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose; In tetrahydrofuran; diethyl ether; at 20 ℃;

DOI:10.1248/cpb.52.727

Reference yield:

(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde (82529-87-1) → (3S,4R,5R,6S)-3,5-di-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene (741256-62-2)

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: 50 percent / aq. H₂SO₄ / tetrahydrofuran / 40 h / 40 °C

4.1: n-BuLi / diethyl ether / 2 h / 20 °C

4.2: 70 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:

1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose (741256-59-7) → (3S,4R,5R,6S)-3,5-di-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene (741256-62-2)

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: 50 percent / aq. H₂SO₄ / tetrahydrofuran / 40 h / 40 °C

3.1: n-BuLi / diethyl ether / 2 h / 20 °C

3.2: 70 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

upstream raw materials:

Methyltriphenylphosphonium bromide

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

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

1,2-O-isopropylidene-3,5-O-di(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose

Downstream raw materials:

D-1,2-di-O-benzyl-myo-inositol

(1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene

(+)-3,5-O-di-(4'-methoxybenzyl)-conduritol B