Cytidine → 2'-O-Pentylcytidine

HRID 1066423Notes

Reaction equation

HRID 1066423 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 (10 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-bdbd6fa57ff94b5a9c76c48876300bd6
Source dataset
uspto-grants-2001_06
Patent number
US06242592B1

Reaction notes

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