Uridine → 2'-O-Nonyluridine

HRID 264734

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-749385ee83504457b5d87e3afcdc281f
Quelldatensatz: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05646265

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