D-Ribofuranose, 1,2,3,5-tetraacetate → 5-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione

HRID 2248945Notes

Reaction equation

HRID 2248945 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[S:10][C:9](=[O:11])[NH:8][C:6]=2[N:7]=1.C(O[CH:17]1[O:29][C@H:28]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])(=O)C>>[NH2:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:17]3[O:29][C@H:28]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]3[O:19][C:20](=[O:22])[CH3:21])[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 9797055D-Ribofuranose, 1,2,3,5-tetraacetateHCID 1357436395-Aminothiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione

Product 1

HCID 1354347855-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione

Procedure

Compound 4 (10 g, 54.4 mmol) was glycosylated exactly as described for the synthesis of 6 except that the sugar used in this case was the 1,2,3,5-tetra-O-acetyl-D-ribofuranose (20.7 g, 65.1 mmol). After the usual workup the crude residue was flash chromatographed on silica gel using 10% methanol in dichloromethane. Yield of pure material 7.1 g (29%) as a dry foam or amorphous solid.

Workup

  1. customchromatographed on silica gel using 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-3f78946843c34a4c86cb1759b52817bd
Source dataset
uspto-grants-1991_08
Patent number
US05041426

Reaction notes

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