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

HRID 744160노트

반응식

HRID 744160 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d552eb4995b43b98421f5a2c583937e
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559101

반응 노트

불러오는 중…