Conversion of uridine 2′,3′-carbonates to anhydrouridines

Ogilvie, Kelvin K.; Iwacha, D.

doi:10.1139/v69-072

Cited by 18 publications

(2 citation statements)

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“…We had noted that a 2',3'-carbonate on a pyrimidine nucleoside is readily displaced by nucleophilic groups on the base ring (34). Further it has been found that there is no need to block either the 5'-hydroxyl or amine groups on the base ring in forming 2',3'-carbonates of purine nucleosides (16,35).…”

Section: Discussion and Resultsmentioning

confidence: 99%

A General Synthesis of 8,2′-Thioanhydropurine Nucleosides

Ogilvie¹,

Slotin²,

Westmore³

et al. 1972

Can. J. Chem.

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The synthesis of 8,2′-anhydro-8-mercapto-9-β-D-arabinofuranosyladenine,8,2′-anhydro-8-mercapto-9-β-D-arabinofuranosylguanine, and 8,2′-anhydro-8-mercapto-9-β-D-arabinofuranosylhypoxanthine is described. The anhydro ring is formed by simultaneous displacement of bromine from position-8 and carbonate from the 2′-position of the parent nucleoside using either sodium hydrogen sulfide or thiourea.

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Section: Discussion and Resultsmentioning

confidence: 99%

A General Synthesis of 8,2′-Thioanhydropurine Nucleosides

Ogilvie¹,

Slotin²,

Westmore³

et al. 1972

Can. J. Chem.

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“…Preparation of Glycosyl Azides.-The per-0-acetyl-/3-D-glycosyl azides la-d were prepared by heating the corresponding per-O-acetyl-a-D-glycosyl halides with sodium azide in dimethylformamide (DMF) by a procedure similar to that used by Yamamoto, et al,10 and Carrington, et al 11 The general procedure is described below.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1-N-Glycosyl-1,2,3-triazoles from Glycosyl Azides and Substituted Acetylenes

Harmon¹,

Earl²,

Gupta³

1971

J. Org. Chem.

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ture was heated under reflux for 3 hr. Most of the methanol was removed (about 200 ml) by distillation and 150 ml of ethyl acetate was added. Potassium chloride was removed (about 15 g) by filtration and was washed several times with ethyl acetate. The combined ethyl acetate solutions were neutralized with saturated NaHCOs solution and were dried over anhydrous magnesium sulfate. Removal of the solvent at reduced pressure yielded the pale yellow ketoxime. A single recrystallization from ligroin afforded 28.3 g (78%) of 3-oximinocamphor, mp 120-123°( reported14 131-133°). The product was used without further purification.2-exo-Hydroxy-3-ezo-aminobornane.-In a 2-1. three-necked flask, equipped with a condenser, a mechanical stirrer, and a dropping funnel, were placed 400 ml of anhydrous ethyl ether (dried over sodium wire) and 21.4 g (0.56 mol) of LiAlH4. After the mixture had been stirred for 15 min, 33.9 g (0.19 mol) of 3-oximinocamphor in 400 ml of anhydrous ethyl ether was added from a dropping funnel at a rate such as to maintain reflux. After being heated under reflux overnight, the mixture was cooled to room temperature and excess L1A1H4 was then destroyed by addition of wet ether, followed by cold water. A white curdy mass of aluminum hydroxide was removed by filtration and was washed several times with ether. The combined ether solutions were dried over anhydrous magnesium sulfate. When the solvent was removed, the residue was distilled under reduced pressure.The product which distilled at 65.1-65.8°( 0.5 mm) solidified and was recrystallized from cold heptane. The yield was 23.6 g (75%), mp 213-214°.

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