Cytidine → 2'-O-Pentylcytidine

HRID 1416715Notes

Reaction equation

HRID 1416715 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CS(C)=O>[CH2:21]([O:3][C@@H:2]1[C@H:4]([OH:5])[C@@H:6]([CH2:7][OH:8])[O:9][C@H:1]1[N:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12])[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 6175CytidineHCID 80571-BromopentaneHCID 24758Sodium hydride

Product 1

HCID 154848952'-O-Pentylcytidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Cytidine (lo g, 0.041 mol), sodium hydride (2.4 g, 1.5 eq), bromopentane (7.6 ml, 1.5 eq.) in DMSO (90 ml) were reacted as per the procedure of Example 71, Step 1 to yield the 2' and 3' isomers as a foam (7.6 g).

Sources & evidence

ORD record
ord-e6c8bcb438b84d1484ee157a8670355b
Source dataset
uspto-grants-1999_06
Patent number
US05914396

Reaction notes

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