Hexamethyldisilazane → HCID 22811363, compound

HRID 1707163Notes

Reaction equation

HRID 1707163 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](=[O:7])[CH2:3][CH:2]=1.C(O[C@@H:12]1[O:34][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)[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:13]1[O:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=O)C.[K].FC(F)(S(O)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.C[Si](N[Si](C)(C)C)(C)C>C(OCC)(=O)C.CO.C(#N)C>[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:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[O:34][C@H:12]1[N:1]1[CH:2]=[CH:3][C:4](=[O:7])[CH:5]=[CH:6]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 13838HexamethyldisilazaneHCID 67815Perfluorobutanesulfonic acidHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 5462222PotassiumHCID 17984897Piridin-4-one

Product 1

HCID 22811363HCID 22811363, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

0.47 g. (5 mmol) of 4-pyridone, 2.52 g. (5 mmol) of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, and 4.06 g. (12 mmol) of the potassium salt of perfluorobutanesulfonic acid were refluxed with 0.29 g. (1.75 mmol) of HMDS and 1.49 g. (13.75 mmol) of TCS in 70 ml. of absolute acetonitrile for 12 hours. The usual working-up step (Example 1) yielded after chromatography on silica gel with ethyl acetate-methanol (95:5) 65% of amorphous 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-pyridone.

Sources & evidence

ORD record
ord-4f1ee4a2544749d498a446c5182f4419
Source dataset
uspto-grants-1980_06
Patent number
US04209613

Reaction notes

Loading…