prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide

Base Information

• Chemical Name: prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide
• CAS No.: 769147-58-2
• Molecular Formula: C₄₄H₆₀N₄O₂₃S
• Molecular Weight: 1045.04
• Mol file: 769147-58-2.mol

Synonyms:

Chemical Property of prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide

There total 10 articles about prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide 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: 48.0%

Trichloroacetyl isocyanate (3019-71-4) + prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-63-9) → prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-58-2)

Guidance literature:

In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/hlca.200490161

Reference yield: 14.6%

p-toluenesulfonyl chloride (98-59-9) + prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-28-6) → prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-58-2)

Guidance literature:

p-toluenesulfonyl chloride; prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide; With pyridine; dmap; at 20 ℃;

With zinc; In methanol; at 20 ℃; for 3h;

DOI:10.1002/hlca.200490161

Reference yield:

3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-4-O-{3,4,6-tri-O-acetyl-2-deoxy-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}-β-D-glucopyranosyl}-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}-1-O-(2,2,2-trichloro-1-iminoethyl)-α-D-glucopyranose (769147-49-1) → prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-58-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 55 percent / Me₃SiOTf / 1,2-dichloro-ethane / 0.75 h / -30 °C

2.1: 63 percent / Zn / 24 h / 20 °C

3.1: 81 percent / NH₃ / tetrahydrofuran; methanol / 3 h / 0 °C

4.1: CH₂Cl₂ / 1 h / 20 °C

4.2: 96 percent / Zn / methanol / 3 h / 20 °C

5.1: 15 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

6.1: DMAP; pyridine / 20 °C

6.2: 14.6 percent / Zn / methanol / 3 h / 20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; zinc; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/hlca.200490161

upstream raw materials:

p-toluenesulfonyl chloride

prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide

Trichloroacetyl isocyanate

prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide