Hydrochloric Acid → 1-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymine

HRID 6778

反応式

HRID 6778 の反応式
C([O:4][C@@H:5]1[C@@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH2:28][O:29]C(=O)C2C=CC=CC=2)([CH2:18][O:19]C(=O)C2C=CC=CC=2)[O:7][C@H:6]1[N:38]1[CH:46]=[C:44]([CH3:45])[C:42](=[O:43])[NH:41][C:39]1=[O:40])(=O)C.C[O-].[Na+].Cl>CO>[CH2:11]([O:10][C@H:9]1[C:8]([CH2:18][OH:19])([CH2:28][OH:29])[O:7][C@@H:6]([N:38]2[CH:46]=[C:44]([CH3:45])[C:42](=[O:43])[NH:41][C:39]2=[O:40])[C@@H:5]1[OH:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 107940411(2-O-Acetyl5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-beta-D-xylofuranosyl)thymineHCID 10942334Sodium Methoxide

生成物 1

HCID 106910381-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymine収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of nucleoside 4 (9.00 g, 0.014 mol) in methanol (130 cm3) was added sodium methoxide (3.87 g, 0.0716 mol). The reaction mixture was stirred at room temperature for 4 h and then neutralised with dilute hydrochloric acid. The mixture was evaporated to dryness under reduced pressure followed by coevaporation using toluene (15 cm3×3). The residue was purified by silica gel column chromatography using dichloromethane/methanol (4–1 5% methanol, v/v) as eluent to give nucleoside triol 5 (4.82 g, 89%) as a white solid material after evaporation of the solvents under reduced pressure.

後処理

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-5bfff2d50122426db511b3e9f2d81ec6
出典データセット
uspto-grants-2006_08
特許番号
US07084125B2

関連ノート

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