4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside
• CAS No.: 500212-98-6
• Molecular Formula: C₃₃H₃₆N₄O₁₅S
• Molecular Weight: 760.733
• Mol file: 500212-98-6.mol

Synonyms:4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside

Chemical Property of 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside

There total 6 articles about 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 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: 57.0%

4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (500212-97-5) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside (500212-98-6)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -30 - -20 ℃; for 2.5h;

DOI:10.1023/A:1020428329743

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride (67817-41-8) → 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside (500212-98-6)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. Na₂CO₃; Bu₄NHSO₄ / ethyl acetate / 40 °C

2: MeONa / methanol

3: 70 mg / (+/-)-camphor-10-sulfonic acid / acetonitrile / 20 °C

4: 57 percent / silver triflate; molecular sieves MS-4 Angstroem / CH₂Cl₂ / 2.5 h / -30 - -20 °C

With 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In methanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1023/A:1020428329743

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside (500212-98-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 mg / (+/-)-camphor-10-sulfonic acid / acetonitrile / 20 °C

2: 57 percent / silver triflate; molecular sieves MS-4 Angstroem / CH₂Cl₂ / 2.5 h / -30 - -20 °C

With 4 A molecular sieve; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1023/A:1020428329743

upstream raw materials:

4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride

benzaldehyde dimethyl acetal

Downstream raw materials:

4-(trichloroacetamido)phenyl 2-deoxy-4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-2-trichloroacetamido-β-D-galactopyranoside

4-nitrophenyl 2-azido-4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside