2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide

Base Information

• Chemical Name: 2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide
• CAS No.: 1378236-20-4
• Molecular Formula: C₃₀H₃₁N₃O₅
• Molecular Weight: 513.593
• Mol file: 1378236-20-4.mol

Synonyms:2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide

Chemical Property of 2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide

There total 7 articles about 2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide 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: 87.0%

propargyl bromide (106-96-7) + 2,3,6-tri-O-benzyl-β-D-galactopyranosyl azide (204510-90-7) → 2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide (1378236-20-4)

Guidance literature:

2,3,6-tri-O-benzyl-β-D-galactopyranosyl azide; With sodium hydride; In N,N-dimethyl-formamide; at -15 ℃; for 0.166667h;

propargyl bromide; In N,N-dimethyl-formamide; at -15 ℃; for 2h;

DOI:10.1002/anie.201201023

Reference yield:

1-amido-1-deoxygalactopyranose (35899-89-9) → 2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide (1378236-20-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / acetonitrile / 24 h / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

3.1: triethylsilane; trifluoroacetic acid; trifluoroacetic anhydride / dichloromethane / 5 h / 0 - 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / -15 °C

4.2: 2 h / -15 °C

With triethylsilane; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201201023

Reference yield:

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-26-2) → 2,3,6-tri-O-benzyl-4-O-propargyl-β-D-galactosylazide (1378236-20-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: methanol; sodium methylate / 20 °C

2.1: toluene-4-sulfonic acid / acetonitrile / 24 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

4.1: triethylsilane; trifluoroacetic acid; trifluoroacetic anhydride / dichloromethane / 5 h / 0 - 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / -15 °C

5.2: 2 h / -15 °C

With methanol; triethylsilane; sodium methylate; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201201023

upstream raw materials:

1-amido-1-deoxygalactopyranose

propargyl bromide

2,3,6-tri-O-benzyl-β-D-galactopyranosyl azide

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

C₆₀H₆₂N₆O₁₀

C₉₀H₉₃N₉O₁₅