3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil

Base Information

• Chemical Name: 3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil
• CAS No.: 80763-42-4
• Molecular Formula: C₂₁H₂₂N₂O₉
• Molecular Weight: 446.414
• Mol file: 80763-42-4.mol

Synonyms:3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil

Chemical Property of 3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil

There total 7 articles about 3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)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: 80.0%

1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose (89195-77-7) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil (80763-42-4) + 1-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil (80541-17-9)

Guidance literature:

With chloro-trimethyl-silane; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1016/0008-6215(83)88357-8

Reference yield:

((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (16831-81-5) → 3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil (80763-42-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.4 g / 4-(dimethylamino)pyridine / pyridine / 16 h / 20 °C

2: conc. H₂SO₄ / acetic acid / 96 h / 20 °C

3: 7 percent / hexamethyldisilazane, chlorotrimethylsilane, tin tetrachloride / acetonitrile / 16 h / 20 °C

With dmap; chloro-trimethyl-silane; sulfuric acid; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; acetic acid; acetonitrile;

DOI:10.1016/0008-6215(83)88357-8

Reference yield:

1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose (35784-67-9) → 3-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil (80763-42-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / aq. acetic acid / 24 h / 20 °C

2: 1.) NaIO₄; 2.) NaBH₄ / 1.) water, 20 deg C, 1 h; 2.) ethanol, 20 deg C, 16 h

3: 85 percent / pyridine / 16 h / 0 °C

4: 1.4 g / 4-(dimethylamino)pyridine / pyridine / 16 h / 20 °C

5: conc. H₂SO₄ / acetic acid / 96 h / 20 °C

6: 7 percent / hexamethyldisilazane, chlorotrimethylsilane, tin tetrachloride / acetonitrile / 16 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; chloro-trimethyl-silane; sulfuric acid; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; acetic acid; acetonitrile;

DOI:10.1016/0008-6215(83)88357-8

upstream raw materials:

1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose

uracil

((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose