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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide
• CAS No.: 769147-52-6
• Molecular Formula: C₅₃H₇₂N₄O₂₁Si
• Molecular Weight: 1129.25
• Mol file: 769147-52-6.mol

Synonyms: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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide

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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide

There total 7 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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-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: 96.0%

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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-26-4) → 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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-52-6)

Guidance literature:

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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide; In dichloromethane; at 20 ℃; for 1h;

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

DOI:10.1002/hlca.200490161

Reference yield:

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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone (769147-50-4) → 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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 81 percent / NH₃ / tetrahydrofuran; methanol / 3 h / 0 °C

2.1: CH₂Cl₂ / 1 h / 20 °C

2.2: 96 percent / Zn / methanol / 3 h / 20 °C

With ammonia; In tetrahydrofuran; methanol; dichloromethane;

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}-α-D-glucopyranose (769147-47-9) → 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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-52-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 1 h / 20 °C

1.2: 88 percent / Cs₂CO₃ / CH₂Cl₂ / 4.5 h / 20 °C

2.1: 55 percent / Me₃SiOTf / 1,2-dichloro-ethane / 0.75 h / -30 °C

3.1: 63 percent / Zn / 24 h / 20 °C

4.1: 81 percent / NH₃ / tetrahydrofuran; methanol / 3 h / 0 °C

5.1: CH₂Cl₂ / 1 h / 20 °C

5.2: 96 percent / Zn / methanol / 3 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; ammonia; zinc; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/hlca.200490161

upstream raw materials:

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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide

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}-α-D-glucopyranose

(tert-butyl)dimethylsilyl 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}-β-D-glucopyranoside

Downstream raw materials:

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

O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-4-O-acetyl-3-O-(aminocarbonyl)-α-D-glucopyranuronamide

O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-1,4-di-O-acetyl-3-O-(aminocarbonyl)-α-D-glucopyranuronamide

O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-α-D-glucopyranuronamide