Tert-Butyl nitrite → 3-(2,3,5-Tri-O-benzoyl-beta-D-Ribofuranosyl)thiazolo[4,5-d] pyrimidine-2,7(6H)-dione
Reaction equation
N[C:2]1[NH:3][C:4](=[O:45])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:34][C@H:33]([CH2:35][O:36][C:37](=[O:44])[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C@@H:23]([O:24][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@H:13]3[O:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]=2[N:7]=1.N(OC(C)(C)C)=O>O1CCCC1>[C:15]([O:14][C@@H:13]1[C@H:23]([O:24][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:33]([CH2:35][O:36][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:34][C@H:12]1[N:8]1[C:6]2[N:7]=[CH:2][NH:3][C:4](=[O:45])[C:5]=2[S:10][C:9]1=[O:11])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Treatment of 6 with sodium methoxide in methanol gave the deprotected guanosine analog, 5-amino-3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (7). When 7 was deaminated with excess nitrous acid the xanthosine analog, 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,5,7(4H,6H)-trione (8) was produced. Replacement of the 5-amino group of compound 6 by a hydrogen atom was accomplished by treatment of 6 with t-butyl nitrite in tetrahydrofuran to yield 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(6H)-dione (9). Deprotection of 9 using sodium methoxide in methanol or methanolic ammonia provided the inosine analog, 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (10).
Sources & evidence
- ORD record
- ord-1bcc7c080de64e349d92b4dd410060f2
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05041426
Reaction notes
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