Azobisisobutyronitrile → 1-[5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2,2-di(phenylthio)-alpha-D-glycero-pentofuranosyl]uracil

HRID 36759Notes

Reaction equation

HRID 36759 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[CH:31][C:29](=[O:30])[NH:28][C:26]2=[O:27])[C:22]([S:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@H:23]([N:25]2[CH:32]=[CH:31][C:29](=[O:30])[NH:28][C:26]2=[O:27])[C:22]([S:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:21]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 111150361-[5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2,2-di(phenylthio)-beta-D-glycero-pentofuranosyl]uracil

Product 1

HCID 152169961-[5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2,2-di(phenylthio)-alpha-D-glycero-pentofuranosyl]uracil

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution prepared by dissolving 7 mg (0.10 mmol) of 1-[5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2,2-di(phenylthio)-β-D-glycero-pentofuranosyl]uracil prepared in step (3) in 10 ml of anhydrous benzene, 150 μl (0.57 mmol) of hydrogenated tributyl tin and 10 mg of azobisisobutylonitrile were added, followed by subjecting the resultant solution to a reflux under heating for 48 hours under an argon gas atmosphere. After completion of the reaction, a low boiling point substances were removed by distillation under a reduced pressure so as to obtain a residue.

Workup

  1. customTo a solution prepared
  2. additionwere added
  3. temperaturea reflux
  4. temperatureunder heating for 48 hours under an argon gas atmosphere
  5. customAfter completion of the reaction
  6. customa low boiling point substances were removed by distillation under a reduced pressure so as
  7. customto obtain a residue

Sources & evidence

ORD record
ord-f798647032db4cd8b9a00f3604fcfd6d
Source dataset
uspto-grants-1995_05
Patent number
US05416204

Reaction notes

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