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

Base Information

• Chemical Name: 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside
• CAS No.: 500212-97-5
• Molecular Formula: C₁₉H₁₈N₄O₆S
• Molecular Weight: 430.441
• Mol file: 500212-97-5.mol

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

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

There total 4 articles about 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-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:

benzaldehyde dimethyl acetal (1125-88-8) + (2R,3R,4R,5R,6S)-5-Azido-2-hydroxymethyl-6-(4-nitro-phenylsulfanyl)-tetrahydro-pyran-3,4-diol → 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (500212-97-5)

Guidance literature:

With camphor-10-sulfonic acid; In acetonitrile; at 20 ℃;

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-1-thio-β-D-galactopyranoside (500212-97-5)

Guidance literature:

Multi-step reaction with 3 steps

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

2: MeONa / methanol

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

With camphor-10-sulfonic acid; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In methanol; ethyl acetate; acetonitrile;

DOI:10.1023/A:1020428329743

Reference yield:

para-nitrobenzenethiol (1849-36-1) → 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (500212-97-5)

Guidance literature:

Multi-step reaction with 3 steps

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

2: MeONa / methanol

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

With camphor-10-sulfonic acid; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In methanol; ethyl acetate; acetonitrile;

DOI:10.1023/A:1020428329743

upstream raw materials:

benzaldehyde dimethyl acetal

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

para-nitrobenzenethiol

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(4-nitro-phenylsulfanyl)-tetrahydro-pyran-4-yl ester

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

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