Triphosphate → 5-Propargylamino-ddUTP

HRID 55718Notes

Reaction equation

HRID 55718 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 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 phsophorus 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%.

Workup

  1. customwas removed
  2. additionAfter addition of the second aliquot of phsophorus 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

Sources & evidence

ORD record
ord-9b3e51c2f8774cfc9b18997f32362e1e
Source dataset
uspto-grants-1997_04
Patent number
US05625081

Reaction notes

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