4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside

Base Information

• Chemical Name: 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside
• CAS No.: 618115-53-0
• Molecular Formula: C₃₂H₄₁N₃O₁₄
• Molecular Weight: 691.689
• Mol file: 618115-53-0.mol

Synonyms:4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside

Chemical Property of 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside

There total 3 articles about 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside 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: 91.0%

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) + 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside (618115-50-7) → 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside (618115-53-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 ℃;

DOI:10.1016/S0008-6215(03)00323-9

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-α/β-D-galactopyranosyl nitrate (196398-25-1) → 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside (618115-53-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Na / 0.5 h / 20 °C

2: 33 percent / PTSA / acetonitrile / 3 h / 0 °C

3: 91 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium; toluene-4-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0008-6215(03)00323-9

Reference yield:

triacetyl-D-galactal (4098-06-0) → 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside (618115-53-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / NaN₃; CAN / acetonitrile

2: Na / 0.5 h / 20 °C

3: 33 percent / PTSA / acetonitrile / 3 h / 0 °C

4: 91 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 0 °C

With sodium azide; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium; toluene-4-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0008-6215(03)00323-9

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside

3,4,6-tri-O-acetyl-2-azido-2-deoxy-α/β-D-galactopyranosyl nitrate

triacetyl-D-galactal

Downstream raw materials:

4-pentenyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)]-α-D-galactopyranoside