9-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine → ((2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydrofuran-2-yl)methyl acetate

HRID 1030773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030773
C(O[C@@H:5]1[C@@H:9](Br)[C@@H:8]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25])(=[O:3])C.C(O[C@@H:30]1[C@@H:34](Br)[C@@H:33]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[O:32][C@H:31]1[N:41]1[CH:49]=[N:48][C:47]2[C:46](=[O:50])[NH:45][CH:44]=[N:43][C:42]1=2)(=O)C.C(O[C@H:55]1[C@@H:59]([CH2:60][O:61][C:62](=[O:64])[CH3:63])[O:58][C@@H:57]([N:65]2[CH:73]=[N:72][C:71]3[C:70](=[O:74])NC=N[C:66]2=3)[C@@H:56]1Br)(=O)C>>[C:13]([O:12][CH2:11][C@H:8]1[O:7][C@@H:6]([N:16]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH2:25])[C:22]=3[N:23]=[CH:24]2)[CH:5]=[CH:9]1)(=[O:15])[CH3:14].[C:38]([O:37][CH2:36][C@H:33]1[O:32][C@@H:31]([N:41]2[C:42]3[N:43]=[CH:44][N:45]=[C:46]([OH:50])[C:47]=3[N:48]=[CH:49]2)[CH:30]=[CH:34]1)(=[O:40])[CH3:39].[C:62]([O:61][CH2:60][C@H:59]1[O:58][C@@H:57]([N:65]2[CH:66]=[CH:71][C:70](=[O:74])[NH:72][C:73]2=[O:3])[CH:56]=[CH:55]1)(=[O:64])[CH3:63]

Komponenten

6

Edukt 3

HCID 109825609-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenineHCID 1354656639-(2,5-Di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)-1,9-dihydro-6H-purin-6-oneHCID 1359761619-(3,5-di-O-acetyl-2-bromo-2-deoxy-beta-D-xylofuranosyl)hypoxanthine

Produkt 3

HCID 11022122((2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydrofuran-2-yl)methyl acetateHCID 11791658((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl acetateHCID 178476336HCID 178476336, Verbindung

Versuchsvorschrift

The reaction conditions were identical to those in Table III but, in addition to 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine, a mixture of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)hypoxanthine and 9-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-xylofuranosyl)hypoxanthine, and 3',5'-O-diacetyl-2'-bromo-2-deoxyuridine were used as substrates to give 5'-O-acetyl-2',3'-didehydro-2',3'-dideoxyadenosine, 5'-O-acetyl-2',3'-didehydro-2',3'-dideoxyinosine and 5'-O-acetyl-2',3'-didehydro-2',3'-dideoxyuridine.

Aufarbeitung

  1. customThe reaction conditions

Quellen und Nachweise

ORD-Eintrag
ord-8ff465a851d74ba99fd6d19e6d87c18a
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106962

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