Trichloroisocyanuric Acid → (2R,4R,5R)-5-((Benzoyloxy)methyl)-3-oxotetrahydrofuran-2,4-diyl dibenzoate

HRID 2059567Notes

Reaction equation

HRID 2059567 reaction equation
[C:1]([O:9][C@H:10]1[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:13]([O:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:11]1[OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.CC1(C)N([O])C(C)(C)CCC1>ClCCl>[C:1]([O:9][C@@H:10]1[C:11](=[O:12])[C@H:13]([O:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:23]([CH2:25][O:26][C:27](=[O:34])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:24]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 11005061alpha-D-Ribofuranose, 1,3,5-tribenzoate

Product 1

HCID 10072943(2R,4R,5R)-5-((Benzoyloxy)methyl)-3-oxotetrahydrofuran-2,4-diyl dibenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3,5-tri-O-benzoyl-α-D-ribofuranose (10.0 g, 21.62 mmol, 1.0 equiv.) is dissolved in dichloromethane (60 ml) and cooled under ice. Trichloroisocyanuric acid (5.52 g, 23.80 mmol, 1.1 equiv.) is added, followed by addition of catalytic amount of TEMPO. The ice bath is removed and the mixture is stirred at room temperature for 1 hour then filtered on Celite®. The organic phase is washed with saturated aqueous Na2CO3 solution, followed by 1N HCl and brine. The organic layer is dried (MgSO4) and the solvent is evaporated to give (2R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-dihydrofuran-3-one as a white foam. 1H-NMR (400 MHz, CDCl3): δ 8.13-8.01 (m, 6H), 7.65-7.37 (m, 9H), 6.20 (d, 1H, J=1.2 Hz), 5.88 (dd, 1H, J=1.2 Hz, 8.8 Hz), 5.05 (m, 1H, J=1.2 Hz, 4 Hz, 8.8 Hz), 4.84 (dd, 1H, J=4 Hz, 12.4 Hz), 4.65 (dd, 1H, J=4 Hz, 12.4 Hz).

Workup

  1. temperaturecooled under ice
  2. customThe ice bath is removed
  3. filtrationthen filtered on Celite®
  4. washThe organic phase is washed with saturated aqueous Na2CO3 solution
  5. dry with materialThe organic layer is dried (MgSO4)
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-680b1b8d2f6448f3b93846e24c0f1488
Source dataset
uspto-grants-2012_10
Patent number
US08278282B2

Reaction notes

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