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5-Fluorouracil → [(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate

HRID 744162
ノート
印刷プレビュー

反応式

HRID 744162 の反応式
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C(O[C@H:14]1[O:36][C@@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:25]([O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:15]1[O:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)C.C[Si](N[Si](C)(C)C)(C)C.Cl[Si](C)(C)C.Cl[Sn](Cl)(Cl)Cl>CC#N>[C:17]([O:16][C@H:15]1[C@@H:25]([O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[O:36][C@@H:14]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 33855-FluorouracilHCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 24287Tin tetrachlorideHCID 10973190Ribofuranose, 1-acetate 2,3,5-tribenzoate

生成物 1

HCID 13827065[(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
収率 61.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a mixture of 5-fluorouracil (0.85 g, 6.54 mmol) and compound 2 (3.0 g, 5.94 mmol) in anhydrous MeCN (100 ml) were successively added HMDS (1.25 ml, 5.95 mmol), ClSiMe3 (0.6 ml, 4.76 mmol) and SnCl4 (0.83 ml, 7.13 mmol). The resulting clear solution was refluxed for 1 hour when TLC indicated completion of the reaction. The solvent was evaporated and the residue dissolved in EtOAc (250 ml), washed with NaHCO3 and H2O. The EtOAc layer was dried, filtered and evaporated to give a white solid and it was crystallized from CHCl3 /MeOH (1-2%) to give compound 5 (2.11 g, 61.9%) as white crystals: m.p. 208°-209° C.

後処理

  1. temperatureThe resulting clear solution was refluxed for 1 hour when TLC
  2. customcompletion of the reaction
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in EtOAc (250 ml)
  5. washwashed with NaHCO3 and H2O
  6. dry with materialThe EtOAc layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customto give a white solid and it
  10. customwas crystallized from CHCl3 /MeOH (1-2%)

出典と根拠

ORDレコード
ord-53dcae0d336b4abab98031f746b383bc
出典データセット
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05559101

反応ノート

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