4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside
• CAS No.: 1259298-28-6
• Molecular Formula: C₁₉H₂₃N₃O₉
• Molecular Weight: 437.406
• Mol file: 1259298-28-6.mol

Synonyms:4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside

Chemical Property of 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside

There total 1 articles about 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-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:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) + 4-methoxy-phenol (150-76-5) → 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside + 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside (1259298-28-6)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 - 20 ℃; optical yield given as %de;

DOI:10.1002/chem.201001204

Reference yield: 92.0%

4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside (1259298-28-6) + benzyl bromide (100-39-0) → 4-methoxyphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside (1401413-70-4)

Guidance literature:

4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside; With 15-crown-5; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201400269

Reference yield: 91.0%

benzaldehyde dimethyl acetal (1125-88-8) + 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside (1259298-28-6) → p-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-azido-α-D-glucopyranoside (1340541-47-0)

Guidance literature:

4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside; With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

benzaldehyde dimethyl acetal; With (1S)-10-camphorsulfonic acid; In N,N-dimethyl-formamide; at 60 - 65 ℃; for 10h; Inert atmosphere;

DOI:10.1021/acs.joc.6b01723

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

4-methoxy-phenol

Downstream raw materials:

4-methoxyphenyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

4-methoxyphenyl (3-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

p-methoxyphenyl 2-azido-4,6-O-benzylidiene-2-deoxy-α-D-glucopyranoside

4-methoxyphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside