2-Fluoroadenine → 9-(2,3,5-Tri-O-benzyl-beta-D-arabinofuranosyl)-2-fluoroadenine

HRID 1646672

Reaktionsgleichung

Reaktionsgleichung von HRID 1646672
[F:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.[CH2:12]([O:19][C@H:20]1[C@H:36]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@@H:35]([CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:34][CH:21]1OC(=O)C1C=CC([N+]([O-])=O)=CC=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:12]([O:19][C@H:20]1[C@H:36]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C@@H:35]([CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:34][C@H:21]1[N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([F:1])=[N:3][C:4]=2[NH2:11])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 127902-FluoroadenineHCID 81531DiisopropylethylamineHCID 970762,3,5-Tri-O-benzyl-1-O-(4-nitrobenzoyl)-D-arabinofuranose

Produkt 1

HCID 109627089-(2,3,5-Tri-O-benzyl-beta-D-arabinofuranosyl)-2-fluoroadenineAusbeute 21,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoroadenine (0.50 g), 2,3,5-tri-O-benzyl-1-α-D-arabinofuranosyl chloride (freshly prepared from 2.22 g of 2,3,5-Tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose) and N,N-diisopropylethylamine (0.56 mL) in anhydrous N,N-dimethylformamide (10 mL) was stirred at ambient temperature for 3 days under a nitrogen atmosphere. The mixture was then concentrated under high vacuum and the residue was partitioned between dichloromethane (200 mL) and water (25 mL). The organic phase was washed sequentially with saturated NaCl (50 mL), 1M H3PO4 (50 mL) and saturated NaCl (25 mL), and was then dried over MgSO4 and decolorizing carbon. The dried solution was filtered and concentrated under vacuum. The residue was purified by silica gel chromotography with 1% methanol in dichloromethane as eluant. The appropriate fractions were combined and recrystalized from ethanol/toluene to obtain 0.39 g of the title compound. This material was identical by IR and TLC with an authentic sample.

Aufarbeitung

  1. concentrationThe mixture was then concentrated under high vacuum
  2. customthe residue was partitioned between dichloromethane (200 mL) and water (25 mL)
  3. washThe organic phase was washed sequentially with saturated NaCl (50 mL), 1M H3PO4 (50 mL) and saturated NaCl (25 mL)
  4. dry with materialwas then dried over MgSO4
  5. filtrationThe dried solution was filtered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel chromotography with 1% methanol in dichloromethane as eluant
  8. customrecrystalized from ethanol/toluene

Quellen und Nachweise

ORD-Eintrag
ord-261ce689ce454fb0a74a6606fe2c6af1
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180824

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