Triphosphate → 5-Propargylamino-ddUTP

HRID 1886509Notes

Reaction equation

HRID 1886509 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-83468ea7a2634d0c9dd8d32d8f389f23
Source dataset
uspto-grants-1992_09
Patent number
US05151507

Reaction notes

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