2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride

Base Information

• Chemical Name: 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride
• CAS No.: 79781-67-2
• Molecular Formula: C₂₇H₂₈ClN₃O₄
• Molecular Weight: 493.99
• Mol file: 79781-67-2.mol

Synonyms:2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride

Chemical Property of 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride

There total 4 articles about 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride 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:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl bromide (79781-71-8) → 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride (79781-67-2)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; In acetonitrile; for 0.15h;

DOI:10.1016/0008-6215(83)88263-9

Reference yield:

1-O-acetyl-2-azido-3,4,6-tri-O-benzyl-2-desoxy-D-galactopyranose (79781-68-3) → 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride (79781-67-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 0.5 M HCl / dioxane / 4 h / Heating

2: pyridine / CH₂Cl₂ / 15 h / 20 °C

3: HBr / CH₂Cl₂ / 5 h / 0 - 5 °C

4: triethylbenzylammonium chloride / acetonitrile

With pyridine; hydrogenchloride; N-benzyl-N,N,N-triethylammonium chloride; hydrogen bromide; In 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1007/BF00949960

Reference yield:

4-Nitro-benzoic acid (3R,4R,5R,6R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (79781-70-7) → 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride (79781-67-2)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr / CH₂Cl₂ / 5 h / 0 - 5 °C

2: triethylbenzylammonium chloride / acetonitrile

With N-benzyl-N,N,N-triethylammonium chloride; hydrogen bromide; In dichloromethane; acetonitrile;

DOI:10.1007/BF00949960

upstream raw materials:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl bromide

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose

1-O-acetyl-2-azido-3,4,6-tri-O-benzyl-2-desoxy-D-galactopyranose

4-Nitro-benzoic acid (3R,4R,5R,6R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Downstream raw materials:

benzyl O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1-3)-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-(1-3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside