2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde

Base Information

• Chemical Name: 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde
• CAS No.: 1443040-53-6
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445
• Mol file: 1443040-53-6.mol

Synonyms:2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde

Chemical Property of 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde

There total 11 articles about 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde 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: 95.0%

methyl 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1443040-52-5) → 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde (1443040-53-6)

Guidance literature:

With diisobutylaluminium hydride;

DOI:10.1021/ml4005039

Reference yield:

1-[(hex-5-yn-1-yloxy)methyl]-4-methoxybenzene (123186-35-6) → 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde (1443040-53-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 0 °C

2.1: triphenylphosphine / phenol / 4 h / 50 °C / Inert atmosphere

3.1: osmium(VIII) oxide; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine / dichloromethane; tert-butyl alcohol; water / 6 h / 0 °C

4.1: pyridine; dmap / dichloromethane / 0.83 h / -78 °C / Inert atmosphere

5.1: triphenylphosphine; triethylamine; formic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / tetrahydrofuran / Reflux; Inert atmosphere

6.1: potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; n-butyllithium; formic acid; methanesulfonamide; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; phenol;

DOI:10.1021/ja404401f

Reference yield:

methyl 7-((4-methoxybenzyl)oxy)hept-2-ynoate (1443040-49-0) → 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde (1443040-53-6)

Guidance literature:

Multi-step reaction with 6 steps

1: triphenylphosphine / phenol / 4 h / 50 °C / Inert atmosphere

2: osmium(VIII) oxide; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine / dichloromethane; tert-butyl alcohol; water / 6 h / 0 °C

3: pyridine; dmap / dichloromethane / 0.83 h / -78 °C / Inert atmosphere

4: triphenylphosphine; triethylamine; formic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / tetrahydrofuran / Reflux; Inert atmosphere

5: potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere

6: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; formic acid; methanesulfonamide; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; phenol;

DOI:10.1021/ja404401f

upstream raw materials:

1-[(hex-5-yn-1-yloxy)methyl]-4-methoxybenzene

methyl 7-((4-methoxybenzyl)oxy)hept-2-ynoate

(2E,4E)-methyl 7-((4-methoxybenzyl)oxy)hepta-2,4-dienoate

(4S,5S,E)-methyl 4,5-dihydroxy-7-((4-methoxybenzyl)oxy)hept-2-enoate

Downstream raw materials:

ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

ethyl 2-((2S,4S,6S)-6-(((2R,4R,6R)-6-(2-oxoethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

ethyl 2-((2S,4S,6S)-6-(((2R,4R,6R)-6-(2-oxoheptadec-3-yn-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate