Cytidine → 2'-O-Pentylcytidine

HRID 368729Notes

Reaction equation

HRID 368729 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-e2f2df44e14547a882e7716ea2a7d8f4
Source dataset
uspto-grants-2000_10
Patent number
US06133438

Reaction notes

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