Thymidine → HCID 6481573, compound

HRID 456341Notes

Reaction equation

HRID 456341 reaction equation
[CH2:1]([O:8]C1C(=O)NC(=O)N(C=1)[C@@H]1O[C@H](CO)[C@@H](O)C1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].[C@@H:27]1([N:35]2[CH:43]=[C:41]([CH3:42])[C:39](=[O:40])[NH:38][C:36]2=[O:37])[O:34][C@H:31]([CH2:32][OH:33])[C@@H:29]([OH:30])[CH2:28]1>C(O)C.[Pd]>[CH2:1]([O:8][CH2:42][C:41]1[C:39](=[O:40])[NH:38][C:36](=[O:37])[N:35]([CH:43]=1)[C@@H:27]1[O:34][C@H:31]([CH2:32][OH:33])[C@@H:29]([OH:30])[CH2:28]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5789ThymidineHCID 67113788HCID 67113788, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 6481573HCID 6481573, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-benzyloxy-2′-deoxyuridine (10 mg) in ethanol (1 mL) was added Pd/C (10%, 10 mg), and the mixture was stirred for five minutes. Hydrogen was introduced to the system via a balloon and the reaction mixture was stirred at room temperature. Aliquots (5 μL) were taken out from the reaction mixture at various time point intervals and were analyzed by thin layer chromatography and HPLC. Complete cleavage to thymidine was observed after ten minutes at room temperature (Scheme 42 and FIG. 4). The intermediate of the cleavage was identified to be 5-hydroxymethyl-dU generated from initial removal of benzyl group, and HOMedU was further reduced to thymidine.

Workup

  1. stirringthe reaction mixture was stirred at room temperature
  2. customremoval of benzyl group, and HOMedU

Sources & evidence

ORD record
ord-267e7b6fe1474c02acddb8eb9ed7ec8d
Source dataset
uspto-grants-2013_07
Patent number
US08497360B2

Reaction notes

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