Phosphorus sulfide (P2S5) → HCID 86749325, compound

HRID 1440007Notes

Reaction equation

HRID 1440007 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=O)[NH:14][C:12]2=[O:13])[CH:8]=[CH:7]1)(=[O:3])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>N1C=CC=CC=1>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[S:21])[NH:14][C:12]2=[O:13])[CH:8]=[CH:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 451499Thymidine, 2',3'-didehydro-3'-deoxy-, 5'-acetate

Product 1

HCID 86749325HCID 86749325, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

MS: m/z 266 (C12H14N2O6, M+), 141 (C7H9O3, sugar group), 126 (C5H6N2O2, base+H). The 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine is dissolved in 25 mL of absolute pyridine and refluxed for 48 hours with 2 g of phosphorus pentasulfide. After cooling, the solution is decanted from the insolubles and evaporated to dryness under vacuum. The resulting residue is fractionated by column chromatography on Kieselgel 40 with chloroform as eluent. From the fractions containing the product, 265 mg of 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-4-thiothymine is obtained after recrystallization from methanol.

Workup

  1. temperatureAfter cooling
  2. customthe solution is decanted from the insolubles
  3. customevaporated to dryness under vacuum
  4. additionFrom the fractions containing the product

Sources & evidence

ORD record
ord-58619e67d1de437d98bac559bcc656cc
Source dataset
uspto-grants-1996_03
Patent number
US05496935

Reaction notes

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