1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose

Base Information

• Chemical Name: 1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose
• CAS No.: 160701-97-3
• Molecular Formula: C₃₂H₃₂N₄O₆S
• Molecular Weight: 600.695
• Mol file: 160701-97-3.mol

Synonyms:1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose

Chemical Property of 1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose

There total 2 articles about 1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose 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-D-galactopyranose (79781-69-4) → 1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose (160701-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 4-Angstroem molecular sieves, pyridinium chlorochromate / CH₂Cl₂ / 0.75 h / Ambient temperature

2: 1.) n-BuLi / 1.) hexane, Et₂O, -78 deg C, 20 min; THF, -78 deg C, 20 min then -78 to -65 deg C, 30 min, 2.) -65 deg C, 1 h

With n-butyllithium; 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/jo00100a050

Reference yield:

2-bromo-1,3-thiazole (3034-53-5,215777-74-5) + acetic anhydride (108-24-7) + (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (160701-84-8) → 1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose (160701-97-3)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) hexane, Et₂O, -78 deg C, 20 min; THF, -78 deg C, 20 min then -78 to -65 deg C, 30 min, 2.) -65 deg C, 1 h;

DOI:10.1021/jo00100a050

Reference yield: 97.0%

1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose (160701-97-3) → 2-(2-Azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)thiazole

Guidance literature:

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; for 0.833333h; Ambient temperature;

DOI:10.1021/jo00100a050

upstream raw materials:

2-bromo-1,3-thiazole

acetic anhydride

(3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

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