Triphosphate → 5-Propargylamino-ddUTP

HRID 728224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728224
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 48 (0.30 mmol) was converted to the corresponding triphosphate and its trifluoroacetyl group was removed following the general procedure given in Example 1E. After addition of the second aliquot of phosphorus oxychloride, phosphorylation was allowed to proceed for a total of 210 min. Assuming an absorption coefficient for the product equal to that of the starting material (13,000), the yield of triphosphate 46, 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. customto proceed for a total of 210 min
  4. customthe yield of triphosphate 46, based on its UV absorption at 291.5 nm

Quellen und Nachweise

ORD-Eintrag
ord-d69c308095014e5cb5e21784229e7a11
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047519

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