phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside

Base Information

• Chemical Name: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside
• CAS No.: 1226524-10-2
• Molecular Formula: C₁₉H₁₉N₃O₄S
• Molecular Weight: 385.444
• Mol file: 1226524-10-2.mol

Synonyms:phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside

There total 5 articles about phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside 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: 81.0%

benzaldehyde dimethyl acetal (1125-88-8) + phenyl-2-azido-2-deoxy-1-thio-D-galactopyranoside (197663-19-7) → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-d-galactopyranoside + phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside (1226524-10-2)

Guidance literature:

With camphor-10-sulfonic acid; In ethylene dibromide; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2012.07.003

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside (197663-12-0) → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-d-galactopyranoside + phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside (1226524-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 20 °C

1.2: Dowex 50W x 8-100 ion exchange resin / pH 7

2.1: toluene-4-sulfonic acid / acetonitrile / 20 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; acetonitrile;

DOI:10.1039/c4ob00128a

Reference yield:

D-(+)-galactosamine hydrochloride (1772-03-8,4710-95-6,6730-09-2,14131-59-0,14131-62-5,14131-63-6,14131-65-8,14131-67-0,14257-79-5,19124-46-0,20706-90-5,91673-92-6) → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-d-galactopyranoside + phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside (1226524-10-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: imidazole-1-sulfonyl azide hydrochloride; copper(II) sulfate; potassium carbonate / methanol / 20 °C

2.1: pyridine

3.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C

4.1: sodium methylate / methanol / 20 °C

4.2: Dowex 50W x 8-100 ion exchange resin / pH 7

5.1: toluene-4-sulfonic acid / acetonitrile / 20 °C

With pyridine; imidazole-1-sulfonyl azide hydrochloride; boron trifluoride diethyl etherate; sodium methylate; potassium carbonate; toluene-4-sulfonic acid; copper(II) sulfate; In methanol; dichloromethane; acetonitrile;

DOI:10.1039/c4ob00128a

upstream raw materials:

benzaldehyde dimethyl acetal

phenyl-2-azido-2-deoxy-1-thio-D-galactopyranoside

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside

D-(+)-galactosamine hydrochloride

Downstream raw materials:

(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol

phenyl 2-azido-6-O-benzyl-3,4-di-O-chloroacetyl-2-deoxy-1-thio-β-D-galactopyranoside