1-Chloro-2-deoxy-3,5-di-o-(p-toluoyl)-alpha-d-erythropentofuranose → 2'-Deoxyimmunosine
Reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:21])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3O)[C:6]=2[N:7]=1.Cl[C@@]1(O[C@H](COC(C2C=CC(C)=CC=2)=O)[C@@H](OC(C2C=CC(C)=CC=2)=O)C1)O>>[NH2:1][C:2]1[NH:3][C:4](=[O:21])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[CH2:13]3)[C:6]=2[N:7]=1Participants
Procedure
The 2'-deoxyerythropentofuranosyl, the xylofuranosyl and the arabinofuranosyl analogs of compound 7 can be prepared in a manner similar to that described for compound 7 (scheme VI). Thus reacting 4 with 1-chloro-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranose followed by deblocking yields 5-amino-3-(2-deoxy-β-D-erythropentofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (36). Likewise after deblocking of the respective intermediates, 4 and 1,2,3,5-tetra-O-acetyl-D-xylofuranose will yield 5-amino-3-(β-D-xylofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (38) and 4 and 1-chloro-2,3,5-tri-O-benzyl-α-D-arabinofuranose will yield 5-amino-3-(β-D-arabinofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (40). The tri-O-acetyl (40) prodrug form of compound 7 is prepared from 4 and 1,2,3,5-tetra-O-acetyl-D-ribofuranose and the 2,3-di-O-isopropylidene derivative (42) is prepared directly from 7 (scheme VI).
Sources & evidence
- ORD record
- ord-5294b1b3c02c4524960502158fa7d659
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05041426
Reaction notes
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