1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil

Base Information

• Chemical Name: 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil
• CAS No.: 80646-93-1
• Molecular Formula: C₁₇H₁₇N₃O₈
• Molecular Weight: 391.337
• Mol file: 80646-93-1.mol

Synonyms:1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil

Chemical Property of 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil

There total 1 articles about 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil 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: 7.8%

benzaldehyde dimethyl acetal (1125-88-8) + 1-(3-nitro-β-D-3-deoxy-glucopyranosyl)-1H-pyrimidine-2,4-dione (4291-56-9) → 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil (80646-93-1) + 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-galactopyranosyl)uracil (84440-77-7)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 50 - 55 ℃; for 32h; under 20 Torr;

DOI:10.1080/07328319608002380

Reference yield: 83.0%

1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil (80646-93-1) → 1-(3'-amino-4',6'-O-benzylidene-3'-deoxy-β-D-glucopyranosyl)uracil (96745-80-1)

Guidance literature:

With hydrogen; nickel; In methanol; water; for 3h; under 2327.2 Torr;

DOI:10.1021/jo00215a013

Reference yield:

1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil (80646-93-1) → 1-(4',6'-O-benzylidene-3'-<(tert-butoxycarbonyl)amino>-3'-deoxy-β-D-glucopyranosyl)uracil (96758-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / H₂ / Raney Ni / methanol; H₂O / 3 h / 2327.2 Torr

2: 79 percent / dimethylformamide; tetrahydrofuran; H₂O / 4 h / Heating

With hydrogen; nickel; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00215a013

upstream raw materials:

benzaldehyde dimethyl acetal

1-(3-nitro-β-D-3-deoxy-glucopyranosyl)-1H-pyrimidine-2,4-dione

Downstream raw materials:

1-(3'-amino-4',6'-O-benzylidene-3'-deoxy-β-D-glucopyranosyl)uracil

1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-arabinohexopyranosyl)uracil

1-(4',6'-O-benzylidene-3'-<(tert-butoxycarbonyl)amino>-3'-deoxy-β-D-glucopyranosyl)uracil

1-(4',6'-O-benzylidene-3'-<(tert-butoxycarbonyl)amino>-3'-deoxy-2'-O-mesyl-β-D-glucopyranosyl)uracil