3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 338744-49-3
• Molecular Formula: C₅₀H₅₇N₃O₁₁
• Molecular Weight: 876.016
• Mol file: 338744-49-3.mol

Synonyms:3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 8 articles about 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-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: 100.0%

3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside → 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (338744-49-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1007/s11426-011-4449-x

Reference yield: 44.0%

benzyl bromide (100-39-0) + 3-chloropropyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (338744-55-1) → 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (338744-49-3)

Guidance literature:

3-chloropropyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside; With sodium azide; In N,N-dimethyl-formamide;

With sodium methylate; In methanol;

benzyl bromide; Further stages;

DOI:10.1002/cbic.201500499

Reference yield:

3-chloropropyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (338744-55-1) → 3-azidopropyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (338744-49-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: KI / dimethylformamide / 0.5 h / 50 °C

1.2: 85 percent / NaN₃ / dimethylformamide / 0.5 h / Heating

2.1: NaOMe / methanol / 16 h / 20 °C

3.1: TMSCl / 3 h / 20 °C

4.1: NaH / dimethylformamide / 1 h / 20 °C

5.1: 733 mg / TFA / CH₂Cl₂; H₂O / 0.08 h / 20 °C

With chloro-trimethyl-silane; sodium methylate; sodium hydride; trifluoroacetic acid; potassium iodide; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo001477w

upstream raw materials:

benzyl bromide

3-chloropropyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

3-azidopropyl (β-O-D-galactopyranosyl)-(1→4)-O-β-D-glucopyranoside

3-azidopropyl (2,3,4,6-tetra-O-acetyl-β-O-D-galactopyranosyl)-(1→4)-O-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

C₇₀H₈₄N₄O₂₃

C₇₀H₈₁Cl₃N₄O₂₃

C₆₉H₈₀N₄O₂₃