Acetone → 2',3'-O-Isopropylideneadenosine

HRID 30502Notes

Reaction equation

HRID 30502 reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].CO[C:22](OC)([CH3:24])[CH3:23].CC(C)=O>CCCCCC>[CH3:23][C:22]1([CH3:24])[O:3][CH:2]2[CH:4]([CH:6]([CH2:7][OH:8])[O:9][CH:1]2[N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:5]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 64952,2-DimethoxypropaneHCID 60961Adenosine

Product 1

HCID 2321792',3'-O-Isopropylideneadenosine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of adenosine (43 g) and 2,2-dimethoxypropane (5 eq.) in acetone (75 eq.) was treated with D-camphorsulphonic acid (1 eq) at and the resulting reaction was allowed to stir for 3 hr. The reaction mixture was concentrated in vacuo and diluted with a mixture of saturated aqueous NaHCO3 (250 mL) and ethyl acetate (250 mL). The resulting solution was transferred to a separatory funnel and the organic layer was separated, dried over sodium sulfate, and concentrated in vacuo to provide a solid residue. The solid residue was suspended in hexane, filtered, washed with hexane and dried to provide 2′,3′-Isopropylidene-adenosine (43 g). 1H NMR (DMSO-d6, 300 MHz): δ 4.12-4.17 (m, 1H), 4.22-4.26 (m, 1H), 4.59 (d, J=4.8 Hz, 1H), 4.74-4.85 (m, 2H), 5.49-5.52 (m, 1H), 5.51 (d, J=5.1 Hz, 1H), 5.84 (d, J=5.1 Hz, 1H), 7.85 (s, 2H), 8.33 (s, 1H). MS m/z 347.11 [M+H]+.

Workup

  1. customthe resulting reaction
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with a mixture of saturated aqueous NaHCO3 (250 mL) and ethyl acetate (250 mL)
  4. customThe resulting solution was transferred to a separatory funnel
  5. customthe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto provide a solid residue
  9. filtrationfiltered
  10. washwashed with hexane
  11. customdried

Sources & evidence

ORD record
ord-82096f8f3d144aaebd4748ff49216b99
Source dataset
uspto-grants-2008_09
Patent number
US07423144B2

Reaction notes

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