N-Benzoylcytidine → HCID 178418385, compound

HRID 1632284Notes

Reaction equation

HRID 1632284 reaction equation
C(NC1C=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=1)(=O)C1C=CC=CC=1.[NH:26]1[C-:30]=[N:29][N:28]=[N:27]1.P([O-])([O-])[O-].[NH:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[C-:43][C:38]=2[N:37]=[N:36]1>C(#N)C>[NH:26]1[CH:30]=[N:29][N:28]=[N:27]1.[NH:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=[N:36]1

Participants

6

Reactant 3

HCID 10066259N-BenzoylcytidineHCID 178420932HCID 178420932, compoundHCID 178527074HCID 178527074, compound

Product 2

HCID 178418385HCID 178418385, compoundHCID 178418441HCID 178418441, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Benzoylcytidine linked from the 3' hydroxyl group via a hemisuccinate bridge to aminopropyl-substituted HPLC-grade silica (Vydac) was used as the solid-phase support. Samples (100 mg each; 10 micromoles) were shaken in sealed test tubes in acetonitrile (1 ml) with each of the four 5'-dimethoxytrityl-deoxynucleoside-3'-dimethylaminophosphoramidites and either tetrazole (1 mmole) or benzotriazole (600 micromoles) to form the tetrazolide or benzotriazolide-phosphite active species, the latter being a compound of this invention. After thorough washing by repeated centrifugation and subsequent decanting, and oxidation with 0.01M iodine, the support was treated with 2.75% (w/v) trichloroacetic acid in methylene chloride (10 ml) for 5 minutes. Spectrophotometric assay of the dimethoxytrityl carbonium ion produced in the supernatant demonstrated that all couplings had proceeded to greater than 95% of theoretical yield.

Sources & evidence

ORD record
ord-a7da0d4ca9bf4f2bab299c45fcc0c396
Source dataset
uspto-grants-1984_10
Patent number
US04474948

Reaction notes

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