4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Base Information

• Chemical Name: 4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• CAS No.: 1312312-41-6
• Molecular Formula: C₂₈H₃₀N₂O₁₂
• Molecular Weight: 586.552
• Mol file: 1312312-41-6.mol

Synonyms:4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Chemical Property of 4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

There total 4 articles about 4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 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: 75.0%

5-nitro-2,3-dihydro-1H-indole (32692-19-6) + (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (287967-74-2) → 4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1312312-41-6)

Guidance literature:

With caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 80 ℃; for 140h; Inert atmosphere;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) → 4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1312312-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylsilyl trifluoromethanesulfonate / toluene / 2.5 h / 20 °C / Inert atmosphere

2: caesium carbonate; XPhos / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 140 h / 80 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → 4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1312312-41-6)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / dichloromethane / 3.5 h / 20 °C / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / toluene / 2.5 h / 20 °C / Inert atmosphere

3: caesium carbonate; XPhos / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 140 h / 80 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In dichloromethane; toluene;

upstream raw materials:

per-O-acetyl-α-D-mannopyranose

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

5-nitro-2,3-dihydro-1H-indole

Downstream raw materials:

4-(5-nitroindolin-1-yl)phenyl α-D-mannopyranoside