Uridine → 2'-O-Propyluridine

HRID 341930Notes

Reaction equation

HRID 341930 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH: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].[CH2:18]([Sn](=O)CCCC)[CH2:19][CH2:20]C.C([C@@]1(O)[C@H](OCCCC)[C@@H](C(=[SnH2])O)O[C@H]1N1C=CC(=O)NC1=O)CCC.ICCC>>[CH2:18]([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](=[O:15])[NH:13][C:11]1=[O:12])[CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 6029UridineHCID 336431-IodopropaneHCID 61221Dibutyltin oxideHCID 1317200902',3'-O-dibutylstannyleneuridine

Product 1

HCID 228747472'-O-Propyluridine

Procedure

As per the procedure of Example 49, uridine (10 g) was treated with dibutyl tin oxide (10.2 g, 1 eq). The resulting 2',3'-O-dibutylstannylene uridine was treated with iodopropane (8 ml, 2 eq.) at 110° C. as per Example 50 to give a mixture of the 2' and 3' isomers (5.5 g) as a foam.

Workup

  1. customto give
  2. additiona mixture of the 2' and 3' isomers (5.5 g) as a foam

Sources & evidence

ORD record
ord-b93f4acf67c847ceb1225cd52d3f00d7
Source dataset
uspto-grants-1999_01
Patent number
US05856466

Reaction notes

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