Methanol → 2',3'-Didehydro-3'-deoxy-4'-ethynylthymidine

HRID 1503306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503306
C(OC([O:8][CH2:9][C@@:10]1([C:24]#[C:25][Si](C)(C)C)[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12]=[CH:11]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].CO.O>C(#N)C>[C:24]([C@:10]1([CH2:9][OH:8])[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12]=[CH:11]1)#[CH:25]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 53372553(2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran

Produkt 1

HCID 30088972',3'-Didehydro-3'-deoxy-4'-ethynylthymidineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(2R,5R)-5-t-Butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran (35 mg) was added to a glass reactor, and the atmosphere of the reactor was changed to nitrogen. To the reactor, potassium carbonate (72 mg) and methanol (3.5 mL) were added, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was mixed with water and acetonitrile so as to form a uniform solution, and the solution was quantitated (LC). The yielded compound was found to be 4′-ethynyl-2′,3′-didehydro-3′-deoxythymidine (yield: 94%, calculated through quantitation) (internal standard: methyl phthalate). The 1H-NMR data of the compound are as follows.

Aufarbeitung

  1. customto form a uniform solution

Quellen und Nachweise

ORD-Eintrag
ord-159b293b6c044f4a8e69bf52ddaa863c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212174B2

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