8-Bromo-2'-deoxyadenosine → HCID 178508654, Verbindung

HRID 2050599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2050599
BrC1N(C2N=CN=C(N)C=2N=1)[C@@H]1O[C@H](CO)[C@@H](O)C1.[SnH](CCCC)(CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C.C[O:46][C:47]1[N:48]([C:56]2[N:57]=[CH:58][N:59]=[C:60]([NH2:63])[C:61]=2[N:62]=1)[C@@H:49]1[O:55][C@H:52]([CH2:53][OH:54])[CH2:51][CH2:50]1>>[OH:46][C:47]1[N:48]([C:56]2[N:57]=[CH:58][N:59]=[C:60]([NH2:63])[C:61]=2[N:62]=1)[C@@H:49]1[O:55][C@H:52]([CH2:53][OH:54])[CH2:51][CH2:50]1

Komponenten

4

Edukt 3

HCID 965478-Bromo-2'-deoxyadenosine2×HCID 146070152',3'-Dideoxy-8-methoxyadenosineHCID 131716885nBu3SnH AIBN

Produkt 1

HCID 178508654HCID 178508654, Verbindung

Versuchsvorschrift

The starting compound for the synthesis of VIII was 8-bromo-2'-deoxyadenosine which was prepared by bromination of the corresponding deoxynucleoside. This starting compound was first converted to its azido derivative and then subjected to the deoxygenation procedure. During the nBu3SnH/AIBN step, reduction of the azido group occurred concomitantly with the deoxygenation. In a related procedure, 8-bromo-2'-deoxyadenosine was converted to the corresponding 8-methoxy compound and then deoxygenated to 2',3'-dideoxy-8-methoxyadenosine (IX). 2',3'-Dideoxy-8-thiomethyl- adenoxine (XI) can be similarly prepared from 8-thiomethyl- 2'-deoxyadenosine. Compound IX can be demethylated to give 2',3'-dideoxy-8-hydroxyadenosine (X).

Aufarbeitung

  1. customdeoxygenated to 2',3'-dideoxy-8-methoxyadenosine (IX)
  2. custom2',3'-Dideoxy-8-thiomethyl- adenoxine (XI) can be similarly prepared from 8-thiomethyl- 2'-deoxyadenosine

Quellen und Nachweise

ORD-Eintrag
ord-12f5066052c243eda1f1ba1c6042ca21
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05013829

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