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 1703732노트

반응식

HRID 1703732 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-083541fcf06a4ad68edddddb140643e1
출처 데이터셋
uspto-grants-1978_11
특허 번호
USRE029835

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