Uridine → 2'-O-Nonyluridine

HRID 341931

Reaktionsgleichung

[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].C([Sn](=O)CCCC)CCC.C([C@@]1(O)[C@H](OCCCC)[C@@H](C(=[SnH2])O)O[C@H]1N1C=CC(=O)NC1=O)CCC.I[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]>>[CH2:55]([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])[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]

Komponenten

Edukt 4

HCID 6029Uridine

HCID 202751-Iodononane

HCID 61221Dibutyltin oxide

HCID 1317200902',3'-O-dibutylstannyleneuridine

Produkt 1

HCID 228747432'-O-Nonyluridine

Versuchsvorschrift

As per the procedure of Example 49, uridine (22.5 g) was treated with dibutyl tin oxide (22.5 g, 1 eq). The resulting 2',3'-O-dibutylstannyleneuridine was treated with iodononane (11 ml, 1.3 eq.) at 130°-140° C. as per Example 50 to give the 2' and 3' isomers (11.2 g) as an oil.

Aufarbeitung

customto give the 2' and 3' isomers (11.2 g) as an oil

Quellen und Nachweise

ORD-Eintrag: ord-3823ff96a32147eca494ad7d119781ac
Quelldatensatz: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05856466

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