1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil

Base Information

• Chemical Name: 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil
• CAS No.: 207683-07-6
• Molecular Formula: C₁₇H₁₅N₃O₇
• Molecular Weight: 373.322

Synonyms:1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil

Chemical Property of 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil

Chemical Property:

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Technology Process of 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil

There total 3 articles about 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)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:

1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil (176895-45-7) → 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil (207683-07-6)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In acetone; at -18 ℃; for 0.416667h;

DOI:10.1080/07328319608002131

Reference yield:

1-((2R,3R,4S,6R)-3,5-Dihydroxy-6-hydroxymethyl-4-nitro-tetrahydro-pyran-2-yl)-1H-pyrimidine-2,4-dione → 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil (207683-07-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / ZnCl₂ / 24 h / Ambient temperature

2: pyridine / 0.67 h / Ambient temperature

With pyridine; zinc(II) chloride;

DOI:10.1080/07328319608002131

Reference yield:

acetic anhydride (108-24-7) + 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil (176895-45-7) → 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl)uracil (207683-07-6) + Acetic acid (2R,4aR,6R,7R,8S,8aS)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:

With pyridine; for 0.666667h; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1080/07328319608002131

upstream raw materials:

acetic anhydride

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

Downstream raw materials:

1-((2R,4aR,6R,7R,8R,8aS)-8-Nitro-2-phenyl-7-pyrrolidin-1-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-1H-pyrimidine-2,4-dione

1-((2R,4aR,6R,7R,8R,8aS)-8-Nitro-2-phenyl-7-piperidin-1-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-1H-pyrimidine-2,4-dione

1-(4,6-O-benzylidene-2,3-dideoxy-2-morpholino-3-nitro-β-D-glucopyranosyl)uracil

1-(2-benzylamino-4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-glucopyranosyl)uracil

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