Triphosphate → 5-Propargylamino-ddUTP

HRID 728224Notes

Reaction equation

HRID 728224 reaction equation
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]

Participants

3

Reactant 2

HCID 3440921TriphosphateHCID 147685415-TFA-ap-ddU

Product 1

HCID 110712025-Propargylamino-ddUTP

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-d69c308095014e5cb5e21784229e7a11
Source dataset
uspto-grants-1991_09
Patent number
US05047519

Reaction notes

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