1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

Base Information

• Chemical Name: 1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene
• CAS No.: 500102-39-6
• Molecular Formula: C₃₃H₃₈O₄
• Molecular Weight: 498.662

Synonyms:1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

Chemical Property of 1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

There total 7 articles about 1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene 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:

benzyl bromide (100-39-0) + (E)-(5S,6S)-6-((E)-Buta-1,3-dienyl)-5-(4-methoxy-benzyloxy)-hept-2-ene-1,7-diol → 1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene (500102-39-6)

Guidance literature:

With sodium hydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(02)01662-3

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → 1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene (500102-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / CSA / 1,2-dichloro-ethane / Heating

2.1: TBAF / tetrahydrofuran

2.2: 87 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂

3.1: 88 percent / LiOH*H₂O; MS 4 Angstroem / tetrahydrofuran / 12 h / Heating

4.1: 90 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 - 20 °C

5.1: NaH / (nBu)4NI / tetrahydrofuran / 12 h / 20 °C

With lithium hydroxide; MS 4 Angstroem; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 2.2: Swern oxidation / 3.1: Horner-Emmons olefination, Bonadies conditions;

DOI:10.1016/S0040-4039(02)01662-3

Reference yield:

(4R,5S)-4-methyl-5-phenyl-3-((2E,4E)-1-oxo-2,4-hexadienyl)-2-oxazolidinone (220944-25-2) → 1-[(E)-(1S,2S)-1-((E)-4-Benzyloxy-but-2-enyl)-2-benzyloxymethyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene (500102-39-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Bu₂BOTf; Et₃N / -78 °C

1.2: LiBH₄ / pH 7

1.3: H₂O₂ / H₂O

2.1: 80 percent / CSA / 1,2-dichloro-ethane / Heating

3.1: TBAF / tetrahydrofuran

3.2: 87 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂

4.1: 88 percent / LiOH*H₂O; MS 4 Angstroem / tetrahydrofuran / 12 h / Heating

5.1: 90 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 - 20 °C

6.1: NaH / (nBu)4NI / tetrahydrofuran / 12 h / 20 °C

With lithium hydroxide; MS 4 Angstroem; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 3.2: Swern oxidation / 4.1: Horner-Emmons olefination, Bonadies conditions;

DOI:10.1016/S0040-4039(02)01662-3

upstream raw materials:

benzyl bromide

p-Anisaldehyde dimethyl acetal

(4R,5S)-4-methyl-5-phenyl-3-((2E,4E)-1-oxo-2,4-hexadienyl)-2-oxazolidinone

[(4S,5S)-5-((E)-Buta-1,3-dienyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetaldehyde

Downstream raw materials:

(4R,4aS,6S,7S,7aS)-7-Benzyloxymethyl-4-methyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[c]pyran-3-one

[(1S,2S,3S,5R)-2-Benzyloxymethyl-5-[1,3]dioxolan-2-ylmethyl-3-(4-methoxy-benzyloxy)-cyclopentyl]-methanol

(4R,4aS,6S,7S,7aS)-7-Benzyloxymethyl-6-(4-methoxy-benzyloxy)-4-methyl-hexahydro-cyclopenta[c]pyran-3-one

(4aR,6S,7S,7aS)-7-Benzyloxymethyl-6-(4-methoxy-benzyloxy)-hexahydro-cyclopenta[c]pyran-3-one

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