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

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 91255-92-4
• Molecular Formula: C₂₃H₂₇NO₁₁
• Molecular Weight: 493.467
• Mol file: 91255-92-4.mol

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-tetrahydro-pyran-3-yl ester 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%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-aminophenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (42011-36-9) + acryloyl chloride (814-68-6,25189-84-8) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-tetrahydro-pyran-3-yl ester (91255-92-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1039/c39910000536

Reference yield:

p-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde (5987-78-0) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-tetrahydro-pyran-3-yl ester (91255-92-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 95 percent / Et₃N / CH₂Cl₂ / 0 °C

With ammonium formate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1039/c39910000536

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acryloylamino-phenoxy)-tetrahydro-pyran-3-yl ester (91255-92-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 95 percent / Et₃N / CH₂Cl₂ / 0 °C

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

DOI:10.1039/c39910000536

upstream raw materials:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-aminophenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

acryloyl chloride

p-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde

4-nitro-phenol

Downstream raw materials:

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