Thymidine → HCID 6481573, compound

HRID 333487Notes

Reaction equation

HRID 333487 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-70cca1d7f6a044f294d4f24365e5c16a
Source dataset
uspto-grants-2014_11
Patent number
US08877905B2

Reaction notes

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