Chlorotrimethylsilane → 2,3,5-tri-O-benzoyl-beta-L-ribofuranosyl pyrimidine

HRID 744160Notes

Reaction equation

HRID 744160 reaction equation
C(O[C@H:5]1[O:27][C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[CH:38]1[CH:43]=[N:42][CH:41]=[N:40][CH:39]=1.C[Si](N[Si](C)(C)C)(C)C.Cl[Si](C)(C)C.Cl[Sn](Cl)(Cl)Cl>CC#N>[C:8]([O:7][C@H:6]1[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:27][C@@H:5]1[C:41]1[N:42]=[CH:43][CH:38]=[CH:39][N:40]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 9260PyrimidineHCID 13838HexamethyldisilazaneHCID 24287Tin tetrachlorideHCID 10973190Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 228656082,3,5-tri-O-benzoyl-beta-L-ribofuranosyl pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (1 mol) and pyrimidine base (1 mol) in anhydrous MeCN are successively added HMDS (1 mol), ClSiMe3 (0.8 mol) and SnCl4 (1.2 mol). The resulting clear solution is refluxed for 1 hour when TLC indicates completion of the reaction. The solvent is evaporated and the residue dissolved in EtOAc, washed with NaHCO3 and H2O. The EtOAc layer is dried, filtered and evaporated to give the crude product, which is either crystallized or purified on a silica gel column to obtain the pure 2,3,5-tri-O-benzoyl-β-L-ribofuranosyl pyrimidine compounds. These compounds are stirred with NH3 /MeOH to give pure β-L-ribofuranosyl pyrimidines after purification and crystallization.

Workup

  1. temperatureThe resulting clear solution is refluxed for 1 hour when TLC
  2. customcompletion of the reaction
  3. customThe solvent is evaporated
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with NaHCO3 and H2O
  6. dry with materialThe EtOAc layer is dried
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude product, which
  10. customeither crystallized
  11. custompurified on a silica gel column

Sources & evidence

ORD record
ord-1d552eb4995b43b98421f5a2c583937e
Source dataset
uspto-grants-1996_09
Patent number
US05559101

Reaction notes

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