1,2,3,5-Tetraacetyl-beta-D-ribofuranose → 1-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carbonitrile

HRID 1703732ノート

反応式

HRID 1703732 の反応式
[C:1]([C:3]1[N:7]=[CH:6][NH:5][N:4]=1)#[N:2].C(O[C@@H:12]1[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]1[O:14][C:15](=[O:17])[CH3:16])(=O)C.P([O-])(OC1C=CC([N+]([O-])=O)=CC=1)(OC1C=CC([N+]([O-])=O)=CC=1)=O>C(Cl)(Cl)Cl>[C:1]([C:3]1[N:7]=[CH:6][N:5]([C@@H:12]2[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]2[O:14][C:15](=[O:17])[CH3:16])[N:4]=1)#[N:2]

参加物

5

反応物 3

HCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 5255575Bis(p-nitrophenyl)-phosphateHCID 178510603HCID 178510603、化合物

生成物 1

HCID 134568011-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carbonitrile

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A mixture of 3-cyano-1,2,4-triazole (9.41 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 150°. Bis(p-nitrophenyl) phosphate (100 mg.) was added with stirring and heating at 150° under diminished pressure was continued for 15 min. The residue was dissolved in chloroform, the solution was filtered and the solvent was removed. Crystallization of the residue from ether provided 28.2 g. (80%) of product with M.P. 96-97°.

後処理

  1. temperaturewas heated in an oil bath
  2. temperaturemaintained at 150°
  3. temperatureheating at 150° under diminished pressure
  4. filtrationthe solution was filtered
  5. customthe solvent was removed
  6. customCrystallization of the residue from ether
  7. customprovided 28.2 g

出典と根拠

ORDレコード
ord-083541fcf06a4ad68edddddb140643e1
出典データセット
uspto-grants-1978_11
特許番号
USRE029835

反応ノート

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