Octanamide → N-Benzoyl-2'-deoxyadenosine

HRID 1385545

Reaktionsgleichung

Reaktionsgleichung von HRID 1385545
C(OC1N=C2C(NC=N2)=C(N)N=1)CCCCCCC.[C:20]([NH:28][C:29]1[C:30]2[N:31]=[CH:32][N:33]([C:45]=2[N:46]=[C:47](C)[N:48]=1)[C@@H:34]1[O:41][C@H:38]([CH2:39][OH:40])[C@@H:36]([OH:37])[C:35]1=S(=O)=O)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)C(C)C)C.C(N)(=O)CCCCCCC>CN(C=O)C>[C:20]([NH:28][C:29]1[C:30]2[N:31]=[CH:32][N:33]([C:45]=2[N:46]=[CH:47][N:48]=1)[C@@H:34]1[O:41][C@H:38]([CH2:39][OH:40])[C@@H:36]([OH:37])[CH2:35]1)(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

6

Edukt 4

HCID 69414OctanamideHCID 81531DiisopropylethylamineHCID 21185088HCID 21185088, VerbindungHCID 86757162HCID 86757162, Verbindung

Produkt 1

HCID 107558N-Benzoyl-2'-deoxyadenosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Synthesis of 5LO sequence 5′-GAA GTC ACT GGA ACG-3′ (SEQ ID NO:21) containing 2-octanoxyadenine at specific positions is described. A solution of N6-benzoyl-2′-deoxy-2-methyl-sulfonyladenosine, ethyl diisopropylamine, octanoylamine, and DMF is heated to 100° C. for 30 min and evaporated to dryness under reduced pressure. Recrystallization of the residue affords N6-benzoyl-2′-deoxyadenosine with the carbon chain in the 2-position. This material is converted by procedures of examples 107 and 108 above into its 5′-DMT-3′-β-cyanoethyldiisopropylphosphoramidite derivative which is inserted into the 5LO-sequence 5′-GAA GTC ACT GGA ACG (SEQ ID NO:21) via automated, solid phase DNA synthesis.

Aufarbeitung

  1. customSynthesis of 5LO sequence 5′-GAA GTC ACT GGA
  2. customevaporated to dryness under reduced pressure
  3. customRecrystallization of the residue

Quellen und Nachweise

ORD-Eintrag
ord-242647b83dd1438b8cb6f4bec6d94260
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262241B1

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