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

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)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide
• CAS No.: 769147-63-9
• Molecular Formula: C₄₃H₅₉N₃O₂₂S
• Molecular Weight: 1002.01
• Mol file: 769147-63-9.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)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-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)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-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)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide

There total 8 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)-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: 40.0%

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)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-61-7) → 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)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃;

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)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-63-9)

Guidance literature:

Multi-step reaction with 6 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: 64 percent / Bu₄NF / tetrahydrofuran / 0.67 h / 20 °C

6.1: 40 percent / DMAP; pyridine / CH₂Cl₂ / 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

Reference yield:

(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 (769147-45-7) → 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)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 55 percent / [PdCl₂(MeCN)2] / acetone / 96 h / 20 °C

2.1: CH₂Cl₂ / 1 h / 20 °C

2.2: 88 percent / Cs₂CO₃ / CH₂Cl₂ / 4.5 h / 20 °C

3.1: 55 percent / Me₃SiOTf / 1,2-dichloro-ethane / 0.75 h / -30 °C

4.1: 63 percent / Zn / 24 h / 20 °C

5.1: 81 percent / NH₃ / tetrahydrofuran; methanol / 3 h / 0 °C

6.1: 64 percent / Bu₄NF / tetrahydrofuran / 0.67 h / 20 °C

7.1: 40 percent / DMAP; pyridine / CH₂Cl₂ / 20 °C

With pyridine; dmap; dichloro bis(acetonitrile) palladium(II); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; zinc; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; acetone;

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)-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