Phosphate → Acetic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

HRID 973280Notes

Reaction equation

HRID 973280 reaction equation
[C:1]([O:4][C@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][CH:22]=[N:23][C:24]=2[NH2:28])(=[O:3])[CH3:2].P([O-])([O-])([O-])=O.C(=O)(O)[O-].[Na+]>>[C:1]([O:4][C@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:14][OH:15])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][CH:22]=[N:23][C:24]=2[NH2:28])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1061PhosphateHCID 9718515830-52-1HCID 516892Sodium Bicarbonate

Product 1

HCID 3008125Acetic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Procedure

To a stirred suspension of 500 mg. of 9-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)adenine (U.S. Pat. No. 3,651,045, supra) in 50 ml. of a 0.1M pH 7 phosphate buffer is added 500 mg. of Bacillus subtilis ATCC 6633 cell paste or lyophilizate (U.S. Pat. No. 3,304,236, Example 9) and the mixture is stirred for 22 hours at 35°-40° C., with periodic addition of saturated aqueous sodium bicarbonate to maintain the pH at 7.0 to 7.5. The incubated mixture is then poured into 150 ml. of methanol and the resulting mixture is filtered through diatomaceous earth and the filtrate evaporated at reduced pressure. The residue is passed through a 1 × 30 cm. column of dry silica gel, and the column is eluted sequentially with 5:95, 10:90 and 20:90 (v/w) methanol-chloroform. The eluate is collected in 10-ml. fractions and those that contain the desired product, as established by thin layer chromatography, are combined and evaporated at reduced pressure to give the desired product 9-(2-O-acetyl-β-D-arabinofuranosyl)adenine; λmaxCH3OH = 259 nm. The structure is confirmed by nmr spectra.

Workup

  1. additionTo a stirred suspension of 500 mg
  2. temperatureto maintain the pH at 7.0 to 7.5
  3. additionThe incubated mixture is then poured into 150 ml
  4. filtrationof methanol and the resulting mixture is filtered through diatomaceous earth
  5. customthe filtrate evaporated at reduced pressure
  6. washcolumn of dry silica gel, and the column is eluted sequentially with 5:95, 10:90 and 20:90 (v/w) methanol-chloroform
  7. customThe eluate is collected in 10-ml
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-ea954078c9034574ba2a10cbecd97a56
Source dataset
uspto-grants-1977_10
Patent number
US04055718

Reaction notes

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