N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide

Base Information

• Chemical Name: N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide
• CAS No.: 135253-89-3
• Molecular Formula: C₂₁H₂₉NO₁₂
• Molecular Weight: 487.461
• Mol file: 135253-89-3.mol

Synonyms:N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide

Chemical Property of N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide

There total 7 articles about N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide 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: 100.0%

Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (135253-86-0) → N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide (135253-89-3)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1039/c39910000536

Reference yield: 95.0%

acryloyl chloride (814-68-6,25189-84-8) + p-Aminophenyl 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside (17691-02-0) → N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide (135253-89-3)

Guidance literature:

With triethylamine; In methanol; at 0 ℃;

DOI:10.1039/c39910000536

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → N-{4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-phenyl}-acrylamide (135253-89-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 57 percent / tetrabutylammonium hydrogen sulphate (TBAHS), 1 M aq. NaOH / CH₂Cl₂ / 25 °C

2: 100 percent / NaOMe / methanol

3: ammonium formate / 10percent Pd/C / methanol / 0.08 h / Heating

4: 95 percent / Et₃N / methanol / 0 °C

With sodium hydroxide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; ammonium formate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1039/c39910000536

upstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

acryloyl chloride

p-Aminophenyl 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside

4-nitrophenyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside