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

Base Information

• Chemical Name: p-methoxyphenyl 2-azido-4,6-O-benzylidiene-2-deoxy-α-D-glucopyranoside
• CAS No.: 1370599-34-0
• Molecular Formula: C₂₀H₂₁N₃O₆
• Molecular Weight: 399.403
• Mol file: 1370599-34-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about p-methoxyphenyl 2-azido-4,6-O-benzylidiene-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: 83.0%

benzaldehyde dimethyl acetal (1125-88-8) + p-methoxyphenyl 2-azido-2-deoxy-α-D-glucopyranoside → p-methoxyphenyl 2-azido-4,6-O-benzylidiene-2-deoxy-α-D-glucopyranoside (1370599-34-0,1340541-47-0)

Guidance literature:

With camphor-10-sulfonic acid; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2013.04.033

Reference yield:

4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside (1259298-28-6) → p-methoxyphenyl 2-azido-4,6-O-benzylidiene-2-deoxy-α-D-glucopyranoside (1370599-34-0,1340541-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 2 h / 20 °C

1.2: Dowex 50W X₈ (H+)

2.1: iodine / acetonitrile / 8 h / 50 °C

With iodine; sodium methylate; In methanol; acetonitrile;

DOI:10.1016/j.carres.2012.01.026

Reference yield: 89.0%

p-methoxyphenyl 2-azido-4,6-O-benzylidiene-2-deoxy-α-D-glucopyranoside (1370599-34-0,1340541-47-0) → C20H21N3O6

Guidance literature:

With di-tert-butyl peroxide; triisopropylsilanethiol; In octane; for 2h; Inert atmosphere; Reflux;

DOI:10.1039/c6ob02670b

upstream raw materials:

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

benzaldehyde dimethyl acetal

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

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

p-methoxyphenyl (2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

p-methoxyphenyl (4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-(1→3)-2-azido-4,6-benzylidene-2-deoxy-α-D-glucopyranoside