Triacetoxyperiodinane → 1-[(2S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-oxo-tetrahydrofuran-2-yl]propyl acetate

HRID 60715Notes

Reaction equation

HRID 60715 reaction equation
[C:1]([O:4][CH:5]([C@@H:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([N:14]2[C:18]3[N:19]=[C:20]([NH2:24])[NH:21][C:22](=[O:23])[C:17]=3[S:16][C:15]2=[O:25])[O:9]1)[CH2:6][CH3:7])(=[O:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1>[C:1]([O:4][CH:5]([C@@H:8]1[CH2:12][C:11](=[O:13])[C@H:10]([N:14]2[C:18]3[N:19]=[C:20]([NH2:24])[NH:21][C:22](=[O:23])[C:17]=3[S:16][C:15]2=[O:25])[O:9]1)[CH2:6][CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1371086961-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl acetate2×

Product 1

HCID 1371087081-[(2S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-oxo-tetrahydrofuran-2-yl]propyl acetateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl acetate (compound 22a, 2.8 g, 7.6 mmol) in THF (100 mL) was added Dess-Martine periodinane (4.8 g, 11.3 mmol). After being stirred at room temperature for 2 hours, the resulting solution was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:10 methanol in DCM) to afford 2.8 g crude product of 1-[(2S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-oxo-tetrahydrofuran-2-yl]propyl acetate (compound 22b). MS obsd. (ESI−) [(M−H)−]: 367.

Workup

  1. filtrationthe resulting solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 1:10 methanol in DCM)

Sources & evidence

ORD record
ord-0a4e26f289ae41db9fbfa5dd76196540
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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