6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid

Base Information

• Chemical Name: 6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid
• CAS No.: 19556-62-8
• Molecular Formula: C₁₂H₁₄N₂O₆
• Molecular Weight: 282.253
• Mol file: 19556-62-8.mol

Synonyms:6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid

Chemical Property of 6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid

There total 2 articles about 6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid 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: 51.0%

5-Bromo-5'-O,6-cyclo-2',3'-O-isopropylideneuridine (114743-18-9) + iodomethylbenzene (620-05-3) → 5-benzyl-2',3'-isopropylidene-O(6),5'-cyclouridine (1160597-04-5) + 6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid (19556-62-8)

Guidance literature:

5-Bromo-5'-O,6-cyclo-2',3'-O-isopropylideneuridine; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

iodomethylbenzene; Further stages;

DOI:10.1016/j.tet.2009.02.077

Reference yield:

2',3'-O-isopropylidene-5-bromouridine (54503-61-6) → 1-(O2,O3-isopropylidene-β-D-ribofuranosyl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid + 2',3'-O-isopropylidene-5-hydroxyuridine (20406-82-0) + 6-hydroxy-2',3'-O-isopropylideneuridine + 6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid (19556-62-8)

Guidance literature:

With sodium hydroxide; at 90.1 ℃; Rate constant; Mechanism; various reagent concentration;

Reference yield: 83.0%

benzyl chloride (100-44-7) + 6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid (19556-62-8) → 6,5'-anhydro-3-benzyl-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid (100928-70-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 5h; Ambient temperature;

DOI:10.1021/jo00359a027

upstream raw materials:

2',3'-O-isopropylidene-5-bromouridine

5-Bromo-5'-O,6-cyclo-2',3'-O-isopropylideneuridine

iodomethylbenzene

Downstream raw materials:

6,5'-anhydro-3-benzyl-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid

O⁶,5'-cyclo-2',3'-O-isopropylidene-5-phenylselenouridine

6,5'-anhydro-3-benzyl-1-β-D-ribofuranosylbarbituric acid

6,3'-anhydro-3-benzyl-1-(5-chloro-5-deoxy-β-D-ribofuranosyl)barbituric acid