Cytidine → 2'-O-Nonylcytidine

HRID 264737Notes

Reaction equation

HRID 264737 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+].I[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CN(C=O)C>[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][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 6175CytidineHCID 202751-IodononaneHCID 24758Sodium hydride

Product 1

HCID 228683932'-O-Nonylcytidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cytidine (10.1 g, 0.0415 mol), sodium hydride (2.0 g, 1.2 eq), iodononane (9.8 ml, 1.2 eq.) in DMF (100 ml) were reacted as per the procedure of Example 71, Step 1 to yield the 2' and 3' isomers as a sticky foam (11.6 g).

Sources & evidence

ORD record
ord-fd8a4e3688574aca93fd2a075c567079
Source dataset
uspto-grants-1997_07
Patent number
US05646265

Reaction notes

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