HCID 54476303, compound → HCID 53730520, compound

HRID 904108Notes

Reaction equation

HRID 904108 reaction equation
[N:1]([C@H:4]1[C@H:8]([O:9]C(=O)C)[C@@H:7]([CH2:13][O:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:6][CH:5]1Cl)=[N+:2]=[N-:3].C[Si]([N:28]([Si](C)(C)C)[C:29]1[CH:34]=[CH:33][NH:32][C:31](=[O:35])[N:30]=1)(C)C>ClCCCl>[N:1]([C@H:4]1[C@H:13]([O:14][C:15](=[O:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@@H:7]([CH2:8][OH:9])[O:6][C@@H:5]1[N:32]1[CH:33]=[CH:34][C:29]([NH2:28])=[N:30][C:31]1=[O:35])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 54476303HCID 54476303, compoundHCID 178504300HCID 178504300, compound

Product 1

HCID 53730520HCID 53730520, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
62.5 °C

Procedure

To a stirred solution of 7.8 g. of 2-azido-2-deoxy-3-O-acetyl-5-O-benzoyl-D-arabinofuranosyl chloride in 300 ml, of 1,2-dichloroethane is added 6 g. of bis(trimethylsilyl) cytosine dissolved in 200 ml. of 1-2-dichloroethane. The solution is stirred at 60-65 degrees C. for 3 days, cooled to room temperature and washed successively with 100 ml. of a saturated NaHCO3 solution and 100 ml. of water. It is then dried and evaporated at reduced pressure at 45 degrees C., and the residue is dissolved in 50 ml. of chloroform. The chloroform solution is applied to a silica-gel column and the β and α anomers are eluted with an acetyl mixture of chloroform and 2-propanol (10:1). The β-anomer, 1-(2-azido-2-deoxy-3-O-acetyl-5-O-benzoyl-β-D-arabinofuranosyl) cytosine, is eluted from the column first, and is obtained after evaporation of the solvent in 37% yield. The α-anomer, 1-(2-azido-2-deoxy-3-O-benzoyl-α-D-arabinofuranosyl) cytosine, is obtained in 10% yield.

Workup

  1. temperaturecooled to room temperature
  2. washwashed successively with 100 ml
  3. customIt is then dried
  4. customevaporated at reduced pressure at 45 degrees C
  5. dissolution, and the residue is dissolved in 50 ml
  6. washthe β and α anomers are eluted with an acetyl mixture of chloroform and 2-propanol (10:1)
  7. washThe β-anomer, 1-(2-azido-2-deoxy-3-O-acetyl-5-O-benzoyl-β-D-arabinofuranosyl) cytosine, is eluted from the column first
  8. customis obtained
  9. customafter evaporation of the solvent in 37% yield

Sources & evidence

ORD record
ord-6e53a13e9f1b4deeb4a3c75e8793df6f
Source dataset
uspto-grants-1980_10
Patent number
US04230698

Reaction notes

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