p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside
• CAS No.: 1333393-48-8
• Molecular Formula: C₂₇H₂₇N₃O₄S
• Molecular Weight: 489.595

Synonyms:p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside

Chemical Property of p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside

There total 3 articles about p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-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:

p-tolyl 4,6-O-benzylidene-2-deoxy-2-azido-1-thio-α-D-galactopyranoside + benzyl bromide (100-39-0) → p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside (1333393-48-8) + p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-α-D-galactopyranoside (1333393-56-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3h;

DOI:10.1002/anie.201100076

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside (1333393-48-8) + p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-α-D-galactopyranoside (1333393-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / acetonitrile / 1 h / 20 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/anie.201100076

Reference yield:

p-tolyl 2-deoxy-2-azido-1-thio-α/β-D-galactopyranoside → p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside (1333393-48-8) + p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-α-D-galactopyranoside (1333393-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / acetonitrile / 1 h / 20 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/anie.201100076

upstream raw materials:

benzyl bromide

benzaldehyde dimethyl acetal

Downstream raw materials:

6-chlorohexyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-D-galactopyranoside

2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

C₄₁H₄₀N₄O₉

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