N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 926624-23-9
• Molecular Formula: C₂₆H₂₈N₂O₉
• Molecular Weight: 512.516

Synonyms:N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Chemical Property of N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide

There total 8 articles about N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide 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:

N-[(2S,3R,4R,5S,6S)-5-Azido-4-hydroxy-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide (861902-56-9) → N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide (926624-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / H₂ / Pd/C / methanol / 4 h / 20 °C

2: molecular sieves 3 Angstroem / methanol / 48 h

With 3 A molecular sieve; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1002/anie.200462150

Reference yield:

2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-(2,2-dimethyl-propionyloxymethyl)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester → N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide (926624-23-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / NaN₃; Bu₄NHSO₄ / dimethylformamide / 16 h / 20 °C

2: 84 percent / MeONa / methanol / 120 h / 20 °C

3: 90 percent / H₂ / Pd/C / methanol / 4 h / 20 °C

4: molecular sieves 3 Angstroem / methanol / 48 h

With sodium azide; 3 A molecular sieve; hydrogen; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.200462150

Reference yield:

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(2,2-dimethyl-propionyloxymethyl)-5-hydroxy-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-4-yl ester (861902-54-7) → N-[(2S,3R,4R,5S,6S)-4-Hydroxy-5-{[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide (926624-23-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / CH₂Cl₂ / 1 h / -15 °C

2.1: NaNO₂ / dimethylformamide / 16 h / 20 °C

2.2: NaHCO₃ / H₂O / 0.08 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 1 h / -15 °C

4.1: 61 percent / NaN₃; Bu₄NHSO₄ / dimethylformamide / 16 h / 20 °C

5.1: 84 percent / MeONa / methanol / 120 h / 20 °C

6.1: 90 percent / H₂ / Pd/C / methanol / 4 h / 20 °C

7.1: molecular sieves 3 Angstroem / methanol / 48 h

With pyridine; sodium azide; 3 A molecular sieve; hydrogen; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium nitrite; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200462150

upstream raw materials:

N-[(2S,3R,4S,5S,6S)-5-Amino-4-hydroxy-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide

vanillin

N-[(2S,3R,4R,5S,6S)-5-Azido-4-hydroxy-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(2,2-dimethyl-propionyloxymethyl)-5-hydroxy-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-4-yl ester

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