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(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate → Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

HRID 1368707
ノート
印刷プレビュー

反応式

HRID 1368707 の反応式
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.C(O[C@H:14]1[O:26][C@@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:15]1[O:16][C:17](=[O:19])[CH3:18])(=O)C>[N+](C1C=CC(OP([O-])(OC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1)([O-])=O.O>[C:17]([O:16][C@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:26][C@@H:14]1[N:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1)(=[O:19])[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 908100(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateHCID 178499122HCID 178499122、化合物

生成物 1

HCID 10691464Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate収率 66%

試薬・触媒・溶媒 2

HCID 5255575Bis(p-nitrophenyl)-phosphate触媒HCID 962Water
溶媒

実験手順

A mixture of methyl 1,2,4-triazole-3-carboxylate (0.64 g, 5 mmol), 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose (2) (1.5 g, 4.72 mmol) and bis(p-nitrophenyl)-phosphate (20 mg) were placed in a pear shaped flask and placed in a preheated oil bath at (160-165° C.). The flask was connected to a water aspirator and kept at 160-165° C. (oil bath temperature) under reduced pressure with stirring for 25 min. The reaction mixture was removed, cooled and diluted with EtOAc (150 mL) and sat. NaHCO3 (100 mL). The product was extracted in EtOAc. The organic extract was washed with water (100 mL) and brine (50 mL), dried and evaporated to dryness. The residue that obtained was purified by flash column of silica gel using CHCl3→EtOAc as the eluent. The pure fractions were collected and evaporated to dryness to give 1.2 g (66%) of pure product: 1H NMR (CDCl3) δ2.10 (3s, 9H, 3 COCH3), 3.98 (s, 3H, OCH3), 4.22 (m, 1H), 4.46 (m, 2H), 5.54 (t, 1H), 5.76 (m, 1H), 6.04 (d, 1H, C1′H), and 8.38 (s, 1H, C3H). Anal. Calc. for C15H19N3O9 (385.22): C, 46.75; H, 4.97; N,10.91. Found: C, 46.82; H, 4.57; N=10.71.

後処理

  1. customwere placed in a pear shaped flask
  2. customplaced in a preheated oil bath at (160-165° C.)
  3. customkept at 160-165° C.
  4. customThe reaction mixture was removed
  5. temperaturecooled
  6. additiondiluted with EtOAc (150 mL) and sat. NaHCO3 (100 mL)
  7. extractionThe product was extracted in EtOAc
  8. extractionThe organic extract
  9. washwas washed with water (100 mL) and brine (50 mL)
  10. customdried
  11. customevaporated to dryness
  12. customThe residue that obtained
  13. customwas purified by flash column of silica gel
  14. customThe pure fractions were collected
  15. customevaporated to dryness

出典と根拠

ORDレコード
ord-f565d3671181431e86fa343ac4dd12da
出典データセット
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06573248B2

反応ノート

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