Thymine → (2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran

HRID 1503305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503305
[C:1]([O:5][C:6]([O:8][CH2:9][C@@:10]1([C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[O:14][C@@H:13](OC(OC(C)(C)C)=O)[CH:12]=[CH:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:29]1[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]1=[O:31]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[C:1]([O:5][C:6]([O:8][CH2:9][C@@:10]1([C:23]#[C:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[O:14][C@@H:13]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH:12]=[CH:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 2

HCID 1135ThymineHCID 53372552(2S,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-t-butoxycarbonyloxy-2,5-dihydrofuran

Produkt 1

HCID 53372553(2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuranAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(2S,5R)-5-t-Butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-t-butoxycarbonyloxy-2,5-dihydrofuran (β/α=>99/1) (2.0 g) was added to a glass reactor, and the atmosphere of the reactor was changed to nitrogen. To the reactor, thymine (3.1 g) and N,N′-dimethylformamide (40 mL) were added under stirring. To the resultant mixture, tetrakis(triphenylphosphine)palladium(0) (560 mg) was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated, and the residue was purified through silica gel column chromatography, to thereby yield 1.6 g of (2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran (yield: 78%, β/α=>99/1). The 1H-NMR data of the compound are as follows.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-07a19624f4794565a60639f039b0b26e
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212174B2

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