1,2,3,5-Tetraacetyl-beta-D-ribofuranose → Methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate

HRID 1703727Notes

Reaction equation

HRID 1703727 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.C(O[C@@H:14]1[O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]1[O:16][C:17](=[O:19])[CH3:18])(=O)C.P([O-])(OC1C=CC([N+]([O-])=O)=CC=1)(OC1C=CC([N+]([O-])=O)=CC=1)=O>C1C=CC=CC=1>[CH3:9][O:8][C:6]([C:3]1[N:4]=[CH:5][N:1]([C@@H:14]2[O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]2[O:16][C:17](=[O:19])[CH3:18])[N:2]=1)=[O:7]

Participants

5

Reactant 3

HCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 5255575Bis(p-nitrophenyl)-phosphateHCID 178499122HCID 178499122, compound

Product 1

HCID 10150551Methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of methyl 1,2,4-triazole-3-carboxylate (12.7 g., 0.10 mol) and 1,2,3,5-tetra-O-acetyl-β -D-ribofuranose (31.8 g., 0.10 mol) was heated in an oil bath maintained at 160-165° until the sugar had melted. Bis(p-nitrophenyl) phosphate (250 mg.) was added and heating at 160-165° was continued with stirring under diminished pressure for 15-20 min. The residue was dissolved in hot benzene, the solution was filtered and cyclohexane was added to the filtrate to give the crystalline product (30.0 g., 77.8%) with M.P. 107-109°.

Workup

  1. temperaturewas heated in an oil bath
  2. temperatureheating at 160-165°
  3. filtrationthe solution was filtered
  4. additioncyclohexane was added to the filtrate
  5. customto give the crystalline product (30.0 g., 77.8%) with M.P. 107-109°

Sources & evidence

ORD record
ord-2b36736c365f497b962f6f812c6cad3f
Source dataset
uspto-grants-1978_11
Patent number
USRE029835

Reaction notes

Loading…