HCID 131719721, compound → HCID 86750012, compound

HRID 1901237Notes

Reaction equation

HRID 1901237 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[O:24][C@H:23]([N:25]2[C:30](=[O:31])[C:29]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[CH:28][NH:27][C:26]2=[O:37])[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[C@H:23]1([N:25]2[C:30](=[O:31])[C:29]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[CH:28][NH:27][C:26]2=[O:37])[O:24][C@H:20]([CH2:19][OH:18])[CH2:21][CH2:22]1

Participants

4

Reactant 1

HCID 131719721HCID 131719721, compound

Product 1

HCID 86750012HCID 86750012, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

1-(2,3-Dideoxy-5- O-tert-butyldiphenylsilyl-α-D-ribofuranosyl-5-(2-thienyl)uracil (0.15 g) was dissolved in tetrahydrofurane, 1M in tetrabutylammonium fluoride (3 ml) and stirred at ambient temperature for 1 hour. The solvent was evaporated and the product was purified by separation on preparative thin layer chromatography (silica-1 mm, ethyl acetate-methanol 9-1) to give 1, (2,3-dideoxy-α-D-ribofuranosyl)-5-(2-thienyl)uracil. TLC (silica, ethyl acetate-methanol 9-1) Rf 0.54.

Workup

  1. customThe solvent was evaporated
  2. customthe product was purified by separation on preparative thin layer chromatography (silica-1 mm, ethyl acetate-methanol 9-1)

Sources & evidence

ORD record
ord-d5aabc7ff561487cb3f698dddc8436c4
Source dataset
uspto-grants-1996_11
Patent number
US05576429

Reaction notes

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