Water → 1-(2-O-Nitro-beta-D-arabinofuranosyl)cytosine

HRID 1906365ノート

反応式

HRID 1906365 の反応式
[N+:1]([O:4][C@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:29]=[CH:28][C:23]([NH:24]C(=O)C)=[N:22][C:20]1=[O:21])([O-:3])=[O:2].C[O-].[Ba+2].C[O-].O>CO>[N+:1]([O:4][C@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:14][OH:15])[O:7][C@H:6]1[N:19]1[CH:29]=[CH:28][C:23]([NH2:24])=[N:22][C:20]1=[O:21])([O-:3])=[O:2]

参加物

5

反応物 3

HCID 962WaterHCID 13438163Barium methanolateHCID 138234091-(2-O-nitro-3,5-di-O-acetyl-beta-D-arabinofuranosyl)-N4-acetylcytosine

生成物 1

HCID 1343641-(2-O-Nitro-beta-D-arabinofuranosyl)cytosine収率 86.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a solution of 1-(2-O-nitro-3,5-di-O-acetyl-β-D-arabinofuranosyl)-N4 -acetylcytosine (10 g., 24 mmol) in anhydrous methanol (425 ml) under an atmosphere of dry nitrogen was added 1.9N barium methoxide (5 ml., 9.5 meq) in methanol. The reaction mixture was stirred at room temperature under an inert atmosphere for one hour and was then neutralized with a cation exchange resin (90 g., Bio-Rex 70/H+, 100-200 mesh )in the presence of water (5 ml). The resin was separated by filtration and washed with methanol. The combined filtrate and washings were evaporated under reduced pressure to yield crude 1-(2-O-nitro-β-D-arabinofuranosyl)cytosine (6.60 g., 95%), which was crystallized from H2O to yield pure 1-(2-O-nitro-β-D-arabinofuranosyl)cytosine (5.97 g., 86%): m.p. 151.3°-152.7° C.;

後処理

  1. customThe resin was separated by filtration
  2. washwashed with methanol
  3. customThe combined filtrate and washings were evaporated under reduced pressure
  4. customto yield crude 1-(2-O-nitro-β-D-arabinofuranosyl)cytosine (6.60 g., 95%), which
  5. customwas crystallized from H2O

出典と根拠

ORDレコード
ord-bc47172fb9ed4514ba1b937dbe8be275
出典データセット
uspto-grants-1987_03
特許番号
US04652554

反応ノート

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