5'-O-tert-Butyldiphenylsilyl-thymidine → 3'-Deoxy-3'-allyl-5'-O-tert-butyldiphenylsilylthymidine
Reaction equation
C(OC[C@@:10]1([N:35]2[CH:43]=[C:41]([CH3:42])[C:39](=[O:40])[NH:38][C:36]2=[O:37])[O:34][C@H:14]([CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:12](O)[CH2:11]1)C1C=CC=CC=1.[Si](OC[C@H]1O[C@@H](N2C=C(C)C(=O)NC2=O)C[C@@H]1O)(C(C)(C)C)(C1C=CC=CC=1)[C:45]1[CH:50]=CC=C[CH:46]=1.C(OC[C@@]1(N2C=C(C)C(=O)NC2=O)O[C@H](CO[Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H](OC(OC2C=CC=CC=2)=S)C1)C1C=CC=CC=1>>[CH2:50]([C@@H:12]1[C@@H:14]([CH2:15][O:16][Si:17]([C:30]([CH3:31])([CH3:32])[CH3:33])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:34][C@@H:10]([N:35]2[CH:43]=[C:41]([CH3:42])[C:39](=[O:40])[NH:38][C:36]2=[O:37])[CH2:11]1)[CH:45]=[CH2:46]Participants
4
Reactant 3
Product 1
Procedure
Utilizing the procedures of Examples 16 and 17 wherein compound 18 was obtained from compound 3 via compound 17, compound 2 is used as the starting material in place of compound 3. Compound 2 is converted via the procedure of Example 16 to an intermediate compound similar to compound 17 except this intermediate differs from compound 17 in that it does not have a blocking group on its heterocyclic base. The intermediate is then treated as per the procedure of Example 17 to give the title compound in 58% yield.
Workup
- additionThe intermediate is then treated as per the procedure of Example 17
Sources & evidence
- ORD record
- ord-7c5c156a31b74c488ec8d1a2c7fb46e3
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05677437
Reaction notes
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