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

Base Information

• Chemical Name: 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
• CAS No.: 769147-56-0
• Molecular Formula: C₄₉H₆₆N₄O₂₂Si
• Molecular Weight: 1091.16
• Mol file: 769147-56-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 67.0%

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 (769147-54-8) → 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 (769147-56-0)

Guidance literature:

With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 20 ℃; for 0.666667h;

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) → 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 (769147-56-0)

Guidance literature:

Multi-step reaction with 8 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

6.1: 94 percent / [Pd(PPh₃)4] / acetic acid / 5 h / 20 °C

7.1: 93 percent / pyridine / 2 h / 20 °C

8.1: 67 percent / hydrazinium acetate / dimethylformamide / 0.67 h / 20 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; ammonia; hydrazinium monoacetate; zinc; In tetrahydrofuran; methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

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) → 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 (769147-56-0)

Guidance literature:

Multi-step reaction with 5 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

3.1: 94 percent / [Pd(PPh₃)4] / acetic acid / 5 h / 20 °C

4.1: 93 percent / pyridine / 2 h / 20 °C

5.1: 67 percent / hydrazinium acetate / dimethylformamide / 0.67 h / 20 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonia; hydrazinium monoacetate; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200490161

upstream raw materials:

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

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

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