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

Base Information

• Chemical Name: 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
• CAS No.: 905456-80-6
• Molecular Formula: C₅₄H₆₄N₂O₁₇S
• Molecular Weight: 1045.17
• Mol file: 905456-80-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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: 100.0%

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) → 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 (905456-80-6)

Guidance literature:

With hydrogen; nickel; In water; isopropyl alcohol; for 3.5h; pH=7;

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) → 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 (905456-80-6)

Guidance literature:

Multi-step reaction with 5 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

5.1: 100 percent / hydrogen / Raney-nickel / propan-2-ol; H₂O / 3.5 h / pH 7

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

DOI:10.1016/j.carres.2006.03.003

Reference yield:

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) → 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 (905456-80-6)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 91 percent / SO₃*NMe₃ / dimethylformamide / 14 h / 20 °C

2.1: 100 percent / hydrogen / Raney-nickel / propan-2-ol; H₂O / 3.5 h / pH 7

With hydrogen; di(n-butyl)tin oxide; nickel; In methanol; water; isopropyl alcohol;

DOI:10.1016/j.carres.2006.03.003

upstream raw materials:

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

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