6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)barbituric acid

Base Information

Chemical Name:6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)barbituric acid
CAS No.:100928-78-7
Molecular Formula:C₁₈H₁₈N₂O₆
Molecular Weight:358.351
Hs Code.:

Synonyms:6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)barbituric acid

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Chemical Property of 6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)barbituric acid

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Technology Process of 6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)barbituric acid

There total 7 articles about 6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)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: 55.0%

: 100928-76-5
6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-chloro-5-deoxy-β-D-arabinofuranosyl)barbituric acid

: 100928-78-7
6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)barbituric acid

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 0.5h; Heating;
DOI:10.1021/jo00359a027

Reference yield:

: 100-44-7
benzyl chloride

: 100928-78-7
6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)barbituric acid

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / DBU / dimethylformamide / 5 h / Ambient temperature

2: 88 percent / 80percent aq. CF₃COOH / 2 h

3: 1.)n-Bu₂SnO / 1.) methanol, reflux, 2.) DMF, RT, 2 h

4: 100 percent / pyridine / 1 h / Ambient temperature

5: 90 percent / LiCl / hexamethylphosphoric acid triamide / 96 h / Ambient temperature

6: 55 percent / 2,2'-azobis(2-methylpropionitrile), n-Bu₃SnH / toluene / 0.5 h / Heating

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium chloride; In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00359a027

Reference yield:

: 100928-71-0
6,5'-anhydro-3-benzyl-1-β-D-ribofuranosylbarbituric acid

: 100928-78-7
6,2'-anhydro-3-benzyl-1-(3-O-acetyl-5-deoxy-β-D-arabinofuranosyl)barbituric acid

Guidance literature:: Multi-step reaction with 4 steps

1: 1.)n-Bu₂SnO / 1.) methanol, reflux, 2.) DMF, RT, 2 h

2: 100 percent / pyridine / 1 h / Ambient temperature

3: 90 percent / LiCl / hexamethylphosphoric acid triamide / 96 h / Ambient temperature

4: 55 percent / 2,2'-azobis(2-methylpropionitrile), n-Bu₃SnH / toluene / 0.5 h / Heating

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; di(n-butyl)tin oxide; lithium chloride; In N,N,N,N,N,N-hexamethylphosphoric triamide; toluene;
DOI:10.1021/jo00359a027