beta-Cyclodextrin → HCID 12081666, compound

HRID 1033286Notes

Reaction equation

HRID 1033286 reaction equation
C(O)[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO.[Br:78][C@@H:79]1[C@@H:83]([CH2:84][O:85][C:86](=[O:88])[CH3:87])[O:82][C@@H:81]([N:89]2[C:98]3[N:97]=[CH:96][N:95]=[C:93]([NH2:94])[C:92]=3[N:91]=[CH:90]2)[C@:80]1(C(=O)C)[OH:99].C(=O)([O-])O.[Na+]>O>[C:86]([O:85][CH2:84][C@H:83]1[O:82][C@@H:81]([N:89]2[C:98]3[N:97]=[CH:96][N:95]=[C:93]([NH2:94])[C:92]=3[N:91]=[CH:90]2)[C@H:80]([OH:99])[C@@H:79]1[Br:78])(=[O:88])[CH3:87]

Participants

5

Reactant 3

HCID 444041beta-CyclodextrinHCID 516892Sodium BicarbonateHCID 67821523HCID 67821523, compound

Product 1

HCID 12081666HCID 12081666, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 50 g of β-cyclodextrin was added to 1 liter of water, the mixture was heated to completely dissolve. The solution was cooled to room temperature and 10 g of 3'-deoxy-3'-bromo-2',5'-O-diacetyladenosine was then added to the solution, and 2.5 g of sodium hydrogencarbonate was added to the mixture over 1 hour. After stirring was continued for further 2 hours, the reaction mixture was extracted 3 times with 500 ml of ethyl acetate. The solvent was distilled off to give 7 g (yield, 78%) of 5'-O-acetyl-3'-deoxy-3'-bromoadenosine

Workup

  1. temperaturethe mixture was heated
  2. dissolutionto completely dissolve
  3. additionwas added to the mixture over 1 hour
  4. extractionthe reaction mixture was extracted 3 times with 500 ml of ethyl acetate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-212cefc3d7094ffea86a60eb075d92e1
Source dataset
uspto-grants-1994_05
Patent number
US05310895

Reaction notes

Loading…