Adenine → HCID 474172, compound

HRID 484378Notes

Reaction equation

HRID 484378 reaction equation
S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[N:12]1[C:20]([NH2:21])=[C:19]2[C:15]([N:16]=[CH:17][NH:18]2)=[N:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[C:46]([O:54][CH2:55][C@H:56]1[O:60][CH2:59][C@H:58]([O:61][S:62]([C:65]2[CH:70]=[CH:69][C:68]([CH3:71])=[CH:67][CH:66]=2)(=[O:64])=[O:63])[CH2:57]1)(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C=O)C.N1C=CC=CC=1>[C:46]([O:54][CH2:55][C@H:56]1[O:60][CH2:59][C@H:58]([O:61][S:62]([C:65]2[CH:66]=[CH:67][C:68]([CH3:71])=[CH:69][CH:70]=2)(=[O:63])=[O:64])[CH2:57]1)(=[O:53])[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1.[NH2:21][C:20]1[N:12]=[CH:13][N:14]=[C:15]2[C:19]=1[N:18]=[CH:17][N:16]2[C@H:58]1[CH2:57][C@@H:56]([CH2:55][OH:54])[O:60][CH2:59]1

Participants

9

Reactant 5

HCID 190AdenineHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 15928749HCID 15928749, compound

Product 2

HCID 474172HCID 474172, compoundHCID 15928749HCID 15928749, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

1,4-Anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol was prepared from 5-benzoyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose by conversion to 5-O-benzoyl-3-deoxy-1-methoxy-α(β)-D-ribofuranose with methanolic HC1, demethoxylation of the latter followed by tosylation of the 2-position with tosyl chloride and pyridine. A mixture of adenine (0.354 g, 2.62 mmol), potassium carbonate (0.362 g, 2.62 mmol), 18-crown-6(0.347 g, 1.31 mmol), and 1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol in DMF (11 mL) was stirred at 75° C. for 11 h. The solvent was removed under reduced pressure. The residue was purified by flash chromatography with 5% MeOH/CHC113 and afforded 0.269 g (0.793 mmol, 60.5%) of the 5'-benzoate of the title compound as a white solid: mp 193°-195° C.; 1H NMR (CDC13): δ2.13-2.22 (m,1H),2.74-2.84 (m,1H),4.12(dd,1H),4.29(dd,1H),4.39-4.50(m,2H),4.59(dd,1H),5.32(m,1H),6.00(s,2H),7.40(t,2H),7.53(t ,1H),7.98(d,1H),8.02(s 1H),8.31(s,1H); UV(MeOH) λmax 260 nm.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by flash chromatography with 5% MeOH/CHC113

Sources & evidence

ORD record
ord-84189e6421bc4358885dfb52e4d59a4e
Source dataset
uspto-grants-1993_07
Patent number
US05231174

Reaction notes

Loading…