p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside

Base Information

• Chemical Name: p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside
• CAS No.: 218617-35-7
• Molecular Formula: C₂₇H₃₉NO₁₇
• Molecular Weight: 649.603
• Mol file: 218617-35-7.mol

Synonyms:p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside

Chemical Property of p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside

There total 6 articles about p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside 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%

acryloyl chloride (814-68-6,25189-84-8) + p-aminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside (251365-49-8) → p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside (218617-35-7)

Guidance literature:

With triethylamine; In methanol; at 0 - 20 ℃; for 2h;

DOI:10.1016/S0040-4039(98)01897-8

Reference yield:

4-nitrophenyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (148705-01-5) → p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside (218617-35-7)

Guidance literature:

Multi-step reaction with 6 steps

1: ethylene glycol; TMSCl / CH₂Cl₂; methanol / 5 h

2: 82 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

3: 62 percent / AgClO₄; SnCl₂ / CH₂Cl₂ / 10 h

4: NaOMe / methanol / 6 h

5: H₂; 10N HCl / 10 percent Pd(OH)2 on carbon / methanol / 6 h / 20 °C

6: 83 percent / Et₃N / methanol / 1.5 h / 20 °C

With hydrogenchloride; dmap; chloro-trimethyl-silane; hydrogen; sodium methylate; silver perchlorate; ethylene glycol; triethylamine; tin(ll) chloride; palladium hydroxide - carbon; In methanol; dichloromethane; 1: Ring cleavage / 2: Acylation / 3: galactosylation / 4: Hydrolysis / 5: Catalytic hydrogenation / 6: Acylation;

DOI:10.1016/S0968-0896(99)00129-7

Reference yield:

p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-β-lactoside (148705-02-6) → p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside (218617-35-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

2: 62 percent / AgClO₄; SnCl₂ / CH₂Cl₂ / 10 h

3: NaOMe / methanol / 6 h

4: H₂; 10N HCl / 10 percent Pd(OH)2 on carbon / methanol / 6 h / 20 °C

5: 83 percent / Et₃N / methanol / 1.5 h / 20 °C

With hydrogenchloride; dmap; hydrogen; sodium methylate; silver perchlorate; triethylamine; tin(ll) chloride; palladium hydroxide - carbon; In methanol; dichloromethane; 1: Acylation / 2: galactosylation / 3: Hydrolysis / 4: Catalytic hydrogenation / 5: Acylation;

DOI:10.1016/S0968-0896(99)00129-7

upstream raw materials:

acryloyl chloride

p-aminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside

p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-β-lactoside

4-nitrophenyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside