Triphosphate → 5-Propargylamino-ddUTP

HRID 975235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 975235
FC(F)(F)C([NH:5][CH2:6][C:7]#[C:8][C:9]1[C:10](=[O:23])[NH:11][C:12](=[O:22])[N:13]([CH:21]=1)[C@@H:14]1[O:20][C@H:17]([CH2:18][OH:19])[CH2:16][CH2:15]1)=O.[O-:26][P:27]([O:30][P:31]([O:34][P:35]([O-])([O-:37])=[O:36])([O-:33])=[O:32])(=[O:29])[O-:28]>>[P:35]([O:19][CH2:18][C@H:17]1[O:20][C@@H:14]([N:13]2[CH:21]=[C:9]([C:8]#[C:7][CH2:6][NH2:5])[C:10](=[O:23])[NH:11][C:12]2=[O:22])[CH2:15][CH2:16]1)([O:34][P:31]([O:30][P:27]([OH:28])([OH:29])=[O:26])([OH:33])=[O:32])(=[O:36])[OH:37]

Komponenten

3

Edukt 2

HCID 3440921TriphosphateHCID 147685415-TFA-ap-ddU

Produkt 1

HCID 110712025-Propargylamino-ddUTP

Versuchsvorschrift

Alkynylamino nucleoside 22 (0.30 mmol) was converted to the corresponding triphosphate and its trifluoroacetyl group was removed following the general procedure given in Example 5E. After addition of the second aliquot of phosphorus oxychloride, phosphorylation was allowed to proceed for 210 minutes. Assuming an absorption coefficient for the product equal to that of the starting material (13,000), the yield of triphosphate 23, based on its UV absorption at 291.5 nm, was 18%.

Aufarbeitung

  1. customwas removed
  2. additionAfter addition of the second aliquot of phosphorus oxychloride, phosphorylation
  3. customAssuming an absorption coefficient for the product equal to that of the starting material (13,000), the yield of triphosphate 23, based on its UV absorption at 291.5 nm

Quellen und Nachweise

ORD-Eintrag
ord-e2e9a1472fae4e94843458f39590cc3e
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05608063

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