Triphosphate → 1-(2-Hydroxyethoxymethyl)5-(3-amino-1-propynyl)cytosine

HRID 728229Notes

Reaction equation

HRID 728229 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:13]=[C:12]([C:14]#[C:15][CH2:16][NH:17]C(=O)C(F)(F)F)[C:10]([NH2:11])=[N:9][C:7]1=[O:8].[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:13]=[C:12]([C:14]#[C:15][CH2:16][NH2:17])[C:10]([NH2:11])=[N:9][C:7]1=[O:8]

Participants

3

Reactant 2

HCID 3440921TriphosphateHCID 199580181-(2-Hydroxyethoxymethyl)-5-(3-trifluoroacetamido-1-propynyl)cytosine

Product 1

HCID 198763381-(2-Hydroxyethoxymethyl)5-(3-amino-1-propynyl)cytosine

Procedure

The hydroxyl group of the sugar part of alkynylamino nucleoside 69 (0.167 mmol) was converted to a triphosphate and the 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 for 75 min. Assuming an absorption coefficient for the product equal to that of the starting material (7,790), the yield of triphosphate 67, based on its UV absorption at 291 nm, was 21%.

Workup

  1. customthe trifluoroacetyl group was removed
  2. additionAfter addition of the second aliquot of phosphorus oxychloride, phosphorylation
  3. customto proceed for for 75 min
  4. customthe yield of triphosphate 67, based on its UV absorption at 291 nm

Sources & evidence

ORD record
ord-f3216508a830439ea7d7bc7668c7cae4
Source dataset
uspto-grants-1991_09
Patent number
US05047519

Reaction notes

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