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

Base Information

• Chemical Name: 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
• CAS No.: 905456-83-9
• Molecular Formula: C₅₄H₆₂N₄O₁₇S
• Molecular Weight: 1071.17
• Mol file: 905456-83-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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-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 (905456-82-8) → 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 (905456-83-9)

Guidance literature:

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; With di(n-butyl)tin oxide; In methanol; at 65 ℃; for 4h;

With trimethyl-sulfo-ammonium betaine; In N,N-dimethyl-formamide; at 20 ℃; for 14h;

DOI:10.1016/j.carres.2006.03.003

Reference yield:

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-[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 (905456-83-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 76 percent / 4 Angstroem molecular sieves; trifluoromethanesulfonic acid; triethylsilane / CH₂Cl₂ / 3 h / -78 °C

2.1: 84 percent / 3 Angstroem molecular sieves; tetrabutylammonium bromide; CuBr₂ / CH₂Cl₂ / 144 h / 20 °C

3.1: 88 percent / Na; methanol / 20 h / 20 °C

4.1: dibutyltin oxide / methanol / 4 h / 65 °C

4.2: 91 percent / SO₃*NMe₃ / dimethylformamide / 14 h / 20 °C

With methanol; triethylsilane; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; tetrabutylammomium bromide; sodium; di(n-butyl)tin oxide; copper(ll) bromide; In methanol; dichloromethane;

DOI:10.1016/j.carres.2006.03.003

Reference yield:

2-acetamido-3-O-[2,3,4-tri-O-acetyl-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 (905456-81-7) → 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 (905456-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / Na; methanol / 20 h / 20 °C

2.1: dibutyltin oxide / methanol / 4 h / 65 °C

2.2: 91 percent / SO₃*NMe₃ / dimethylformamide / 14 h / 20 °C

With methanol; sodium; di(n-butyl)tin oxide; In methanol;

DOI:10.1016/j.carres.2006.03.003

upstream raw materials:

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

2-acetamido-3-O-[2,3,4-tri-O-acetyl-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

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

Downstream raw materials:

Sulfuric acid mono-{(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5S,6R)-3-acetylamino-2-amino-6-benzyloxymethyl-5-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-3,5-dihydroxy-tetrahydro-pyran-4-yl} ester