p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

Base Information

• Chemical Name: p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside
• CAS No.: 359689-81-9
• Molecular Formula: C₄₁H₅₁NO₂₆
• Molecular Weight: 973.847
• Mol file: 359689-81-9.mol

Synonyms:p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

Chemical Property of p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

There total 1 articles about p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside 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: 94.9%

acetic anhydride (108-24-7) + p-nitrophenyl O-β-D-galactopyranosyl-(1->3)-O-(6-O-acetyl-β-D-galactopyranosyl)-(1->4)-β-D-xylopyranoside (182925-05-9) → p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (359689-81-9)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1246/bcsj.74.1123

Reference yield:

acetic anhydride (108-24-7) + p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (359689-81-9) → Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-[(3R,4S,5R,6S)-4,5-diacetoxy-6-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yloxy]-4-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:

With hydrogen; under 5320 Torr;

DOI:10.1016/S0040-4039(96)01462-1

Reference yield:

p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (359689-81-9) → N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->3)-L-serine benzyl ester (182925-07-1)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen / Pd / 48 h / 20 °C / 5320 Torr

2: 33.5 mg / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 0.33 h

3: Cs₂CO₃ / CH₂Cl₂ / 1.5 h

4: 41.5 mg / trimethylsilyl triflate; molecular sieves 4A / 1,2-dichloro-ethane / 3 h

With ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; caesium carbonate; palladium; In dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1246/bcsj.74.1123

upstream raw materials:

acetic anhydride

p-nitrophenyl O-β-D-galactopyranosyl-(1->3)-O-(6-O-acetyl-β-D-galactopyranosyl)-(1->4)-β-D-xylopyranoside

Downstream raw materials:

N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->3)-L-serine benzyl ester