2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide

Base Information

• Chemical Name: 2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide
• CAS No.: 290330-37-9
• Molecular Formula: C₃₄H₄₀N₄O₁₃
• Molecular Weight: 712.711
• Mol file: 290330-37-9.mol

Synonyms:2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide

Chemical Property of 2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide

There total 2 articles about 2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide 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: 97.0%

4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranosylazide (168397-51-1) + 2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide (290330-34-6) → 2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (290330-37-9)

Guidance literature:

With 3 A molecular sieve; mercury(II) cyanide; In dichloromethane; 1,2-dichloro-ethane; at 20 ℃; for 144h;

DOI:10.1016/j.carres.2006.03.003

Reference yield:

1,2,3,4-tetra-O-acetyl- 6-O-benzyl-α/β-D-galactopyranoside (196942-01-5) → 2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (290330-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: TMSBr; BiBr₃

2: 97 percent / Hg(CN)2; 3 Angstroem molecular sieves / CH₂Cl₂; 1,2-dichloro-ethane / 144 h / 20 °C

With bismuth(III) bromide; trimethylsilyl bromide; 3 A molecular sieve; mercury(II) cyanide; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.carres.2006.03.003

Reference yield: 76.0%

2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (290330-37-9) → 2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide (290330-40-4)

Guidance literature:

With triethylsilane; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -78 ℃; for 3h;

DOI:10.1016/j.carres.2006.03.003

upstream raw materials:

4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranosylazide

2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide

1,2,3,4-tetra-O-acetyl- 6-O-benzyl-α/β-D-galactopyranoside

Downstream raw materials:

2-acetamido-3-O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

N-[(2R,3R,4R,5S,6R)-2-Amino-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-5-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

2-acetamido-3-O-[6-O-benzyl-3-O-sulfatyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl azide