1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate
• CAS No.: 945626-48-2
• Molecular Formula: C₄₁H₃₉Cl₃N₄O₁₆
• Molecular Weight: 950.137
• Mol file: 945626-48-2.mol

Synonyms:1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate

Chemical Property of 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate

There total 7 articles about 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate 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: 78.0%

O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranoside + trichloroacetonitrile (545-06-2) → 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate (945626-48-2)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃;

DOI:10.1039/b618662a

Reference yield:

phenyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside (945626-51-7) → 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate (945626-48-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / sym-collidine; silver triflate / CH₂Cl₂ / 2 h / -30 °C

2: 90 percent / NBS; H₂O / tetrahydrofuran / 0.5 h / 20 °C

3: 78 percent / K₂CO₃ / CH₂Cl₂ / 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; water; silver trifluoromethanesulfonate; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b618662a

Reference yield:

phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside (945626-52-8) → 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate (945626-48-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NBS; H₂O / tetrahydrofuran / 0.5 h / 20 °C

2: 78 percent / K₂CO₃ / CH₂Cl₂ / 20 °C

With N-Bromosuccinimide; water; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b618662a

upstream raw materials:

trichloroacetonitrile

phenyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Acetic acid (2R,3S,4R,5R,6R)-4-acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yl ester