1-Butanol → Tri-O-acetylguanosine

HRID 1378710Notes

Reaction equation

HRID 1378710 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C@@H:8]1([N:17]2[C:27]3[N:26]=[C:24]([NH2:25])[NH:23][C:21](=[O:22])[C:20]=3[N:19]=[CH:18]2)[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[C@H:9]1[OH:10].C(N(CC)CC)C.[C:35](OCC)(=[O:37])[CH3:36].[CH2:41]([OH:45])[CH2:42]CC>CN(C)C1C=CN=CC=1.C(#N)C.CN(C=O)C>[C:35]([O:10][C@@H:9]1[C@H:11]([O:12][C:41](=[O:45])[CH3:42])[C@@H:13]([CH2:14][O:15][C:5](=[O:7])[CH3:6])[O:16][C@H:8]1[N:17]1[C:27]2[N:26]=[C:24]([NH2:25])[NH:23][C:21](=[O:22])[C:20]=2[N:19]=[CH:18]1)(=[O:37])[CH3:36]

Participants

9

Reactant 5

HCID 2631-ButanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 135398635Guanosine

Product 1

HCID 135465084Tri-O-acetylguanosine

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Acetic anhydride (89.3 mL, 0.95 mol) was added rapidly to a magnetically stirred suspension of anhydrous guanosine (76.56 g, 0.27 mol), 4-dimethylaminopyridine (DMAP, 2.47 g, 0.02 mol), and triethylamine (TEA, 149 mL, 1.07 mol) in acetonitrile (500 mL, synthesis grade). The mixture was stirred magnetically, and, after a short induction period, a substantial exotherm was observed as the temperature of the mixture rose to about 50° C. Within 3-5 minutes, the mixture became a faintly cloudy solution. This solution was stirred for 30 minutes, at which time TLC (silica gel plates eluted with 6:3:1 ethyl acetate:DMF:1-butanol) showed only the title compound and a trace of N2 -acetyl-2',3',5'-tri-O-acetylguanosine at higher Rf and DMAP at very low Rf.

Workup

  1. customrose to about 50° C

Sources & evidence

ORD record
ord-a0a076ed32b14f9591da733178434d78
Source dataset
uspto-grants-1997_09
Patent number
US05668270

Reaction notes

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