A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 247-250

  Choudhury, Anusuya ^a,b   Jin, Fuqiang ^a   Wang, Dengjin ^a   Wang, Zhe ^a   Xu, Guoyou ^a   Nguyen, Dieu ^a   Castoro, John ^a   Pierce, Michael E ^a   Confalone, Pat N ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b JOHNSON AND JOHNSON   (United States)

Author keywords

hydroxylactone; fluorolactone; Nucleosides; Purines

Indexed keywords

DIHYDRO 5 (HYDROXYMETHYL) 2(3H) FURANONE; FLUOROLACTONE; FURANONE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ANTIVIRAL ACTIVITY; ARTICLE; BROMINATION; DEPROTECTION REACTION; DRUG SYNTHESIS; FLUORINATION; GLYCOSYLATION; STEREOCHEMISTRY;

EID: 0037421093     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02532-7     Document Type: Article

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30. 3 (50 mg) followed by TMSBr (1.3 mL). The solution was stirred in ice bath until the absence of 7 was observed by TLC. The mixture was quenched with saturated aqueous sodium bicarbonate then washed with and finally water. The solution was concentrated in vacuo to give crude 8 (1.03 g) as an oil. Separately 6-chloropurine (760 mg, 8.3 mmol) and ammonium sulfate (20 mg) were suspended in 20 mL of hexamethyldisilazane, heated to reflux and held for 3 h. The solution was concentrated in vacuo to a crude solid which was dissolved in dichromethane (8 mL) and treated with crude bromide 8. After stirring overnight at rt the mixture was concentrated in vacuo then chromatographed on silica gel with EtOAc/hexane to give compound 9 (400 mg, 34%) as a white solid.