6979-97-1 → Thymidine

HRID 234777Notes

Reaction equation

HRID 234777 reaction equation
C([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11]C(=O)C)[O:8][C@@H:7]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:6]1)(=O)C.[Na]>CO>[CH3:22][C:21]1[C:19](=[O:20])[NH:18][C:16](=[O:17])[N:15]([C@@H:7]2[O:8][C@H:9]([CH2:10][OH:11])[C@@H:5]([OH:4])[CH2:6]2)[CH:23]=1

Participants

4

Reactant 2

HCID 27243486979-97-1HCID 5360545Sodium

Product 1

HCID 5789ThymidineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 3',5'-di-O-acetylthymidine was dissolved in 20 ml methanol, and 0.075 gm sodium was added. After 8 hrs the reaction was quenched with Amberlite IR 120 resin, filtered and concentrated to yield beta-thymidine (2.4 gm, 80%). m.p. 181°-183° C.

Workup

  1. customAfter 8 hrs the reaction was quenched with Amberlite IR 120 resin
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4cc11fb97f7d47c7a671f334bcbab49a
Source dataset
uspto-grants-1997_01
Patent number
US05596087

Reaction notes

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