1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose

Base Information

• Chemical Name: 1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose
• CAS No.: 99748-10-4
• Molecular Formula: C₂₁H₂₃NO₁₄
• Molecular Weight: 513.412
• Mol file: 99748-10-4.mol

Synonyms:1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose

Chemical Property of 1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose

There total 10 articles about 1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose 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: 92.0%

1,2,4,6-tetra-O-acetyl-α-D-mannopyranose (65877-60-3) + 4-Nitrophenyl chloroformate (7693-46-1) → 1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose (99748-10-4)

Guidance literature:

With pyridine; dmap; at 40 ℃; for 2h; Inert atmosphere;

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-mannopyranoside (65827-58-9) → 1,2,4,6-tetra-O-acetyl-3-O-((p-nitrophenyl)carbamoyl)-α-D-mannopyranose (99748-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / H₂ / 10percent Pd(OH)2/C / methanol / 10 h / 25 °C / 760 Torr

2: 86 percent / pyridine, DMAP / 2 h / 40 °C

With pyridine; dmap; hydrogen; palladium dihydroxide; In methanol;

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-mannopyranoside (65827-58-9) → Acetic acid (2R,3R,5S,6R)-5,6-diacetoxy-2-acetoxymethyl-4-(4-nitro-phenoxycarbonyloxy)-tetrahydro-pyran-3-yl ester (99748-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / H₂ / 10percent Pd/C / ethyl acetate / 14 h / 25 °C / 760 Torr

2: pyridine, (N,N-dimethylamino)pyridine / 20 h / 25 °C

With pyridine; dmap; hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1021/jo00352a012

upstream raw materials:

1,2,4,6-tetra-O-acetyl-α-D-mannopyranose

4-Nitrophenyl chloroformate

1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-mannopyranoside

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

Downstream raw materials:

1,3,4,5-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside

(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-4-(carbamoyloxy)-6-(((2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(acetoxymethyl)-2-(2-(2-(((benzyloxy)carbonyl)amino)ethoxy)ethoxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate

3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

1,3,4,6-tetra-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranoside