Cytidine → 2'-O-Nonylcytidine

HRID 1416713Notes

Reaction equation

HRID 1416713 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-04ac80e407194e7a977ef9e2850b3a1b
Source dataset
uspto-grants-1999_06
Patent number
US05914396

Reaction notes

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