Diastereocontrolled electrophilic fluorinations of 2-deoxyribonolactone: Syntheses of all corresponding 2-deoxy-2-fluorolactones and 2′-deoxy- 2′-fluoro-NAD+s

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 5779-5789

  Cen, Yana ^a   Sauve, Anthony A ^a  

^a WEILL CORNELL MEDICAL COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUNDS; FLUORINE; HALOGENATION; SILANES; SUGAR (SUCROSE); SUGARS;

2-DEOXY-2; 2-DEOXYRIBONOLACTONE; AIR-STABLE; CHEMICAL EQUATIONS; CHEMICAL YIELDS; DINUCLEOTIDES; DIRECTIVE EFFECT; EFFICIENT METHOD; ELECTROPHILIC FLUORINATION; ENOLATES; FLUORINATED PRODUCTS; FLUORINATING AGENTS; HIGH YIELD; ISOLATED YIELD; PROTECTING GROUP; SIGNALING PROCESS; SILYLATIONS; STARTING MATERIALS; TRIMETHYLSILYL GROUPS;

FLUORINATION;

1 (2 DEOXY 2 FLUORO DEXTRO RIBOFURANOSYL)NICOTINAMIDE; 1 (2' DEOXY 2' FLUOROARABINOFURANOSYL)NICOTINAMIDE; 1 (2' DEOXY 2',2' DIFLUORORIBOFURANOSYL)NICOTINAMIDE; 1 CHLORO 2 DEOXY 2 FLUORO 3,5 DI O(TERT BUTYLDIMETHYLSILYL)DEXTRO RIBOFURANOSE; 1 CHLORO 2 DEOXY 2 FLUORO 3,5 DI O(TRIISOPROPYLSILYL)DEXTRO ARABINOFURANOSE; 1 METHYLSULFONYL 2 DEOXY 2,2 DIFLUORO 3,5 DI O(TRIISOPROPYLSILYL)DEXTRO RIBOFURANOSE; 1 [2' DEOXY 2 ' FLUORO 3',5' DI O(TRIISOPROPYLSILYL)ARABINOFURANOSYL]NICOTINAMIDE; 1 [2' DEOXY 2' FLUORO 3',5' DI O(TERT BUTYLDIMETHYLSILYL)DEXTRO RIBOFURANOSYL]NICOTINAMIDE; 1 [2' DEOXY 2',2' DIFLUORO 3',5' DI O(TRIISOPROPYLSILYL)RIBOFURANOSYL]NICOTINAMIDE; 2 DEOXY 2 BROMO 2 FLUORO 3,5 DI O(TERT BUTYLDIMETHYLSILYL)DEXTRO RIBONOLACTONE; 2 DEOXY 2 BROMO 3,5 DI O(TERT BUTYLDIMETHYLSILYL)DEXTRO RIBONO,ARABINO LACTONE; 2 DEOXY 2 FLUORO 3,5 DI O(TERT BUTYLDIMETHYLSILYL)DEXTRO RIBONOFURANOSE; 2 DEOXY 2 FLUORO 3,5 DI O(TERT BUTYLDIMETHYLSILYL)DEXTRO RIBONOLACTONE; 2 DEOXY 2 FLUORO 3,5 DI O(TRIIOSOPROPYLSILYL)DEXTRO ARABINOFURANOSE; 2 DEOXY 2 TRIMETHYLSILYL 3,4 DI O(TERT BUTYLDIMETHYLSILYL)DEXTRO ARABINOLACTONE; 2 DEOXY 2,2 DIFLUORO 3,5 DI O(TRIISOPROPYLSILYL)DEXTRO RIBOFURANOSE; 2 DEOXY 2,2 DIFLUORO 3,5 DI O(TRIISOPROPYLSILYL)DEXTRO RIBONOLACTONE; 2 DEOXY 3,5 DI O(PENTO CHLOROBENZOYL)DEXTRO RIBONOLACTONE; 2 DEOXY 3,5 DI O(TERT BUTYLDIMETHYLSILYL)DEXTRO RIBONOLACTONE; 2 DEOXY 3,5 DI O(TRIISOPROPYLSILYL)DEXTRO RIBONOLACTONE; 2 DEOXY FLUORO 2 FLUORO 3,5 DI O(TRIISOPROPYLSILYL)DEXTRO RIBONOLACTONE; 2' DEOXY 2' FLUOROARABINONICOTINAMIDE MONONUCLEOTIDE; 2' DEOXY 2' FLUORORIBONICOTINAMIDE MONONUCLEOTIDE; 2' DEOXY 2',2' DIFLUORORIBONICOTINAMIDE MONONUCLEOTIDE; 4 HYDROXYMETHYL 2 BUTEN 4 OLIDE; 4 [(TERT BUTYLDIMETHYLSILOXY)METHYL] 4 FLUORO 2 BUTEN 4 OLIDE; ELECTROPHILE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; 2,4,5-TRIHYDROXYPENTANOIC ACID GAMMA-LACTONE; LACTONE; NICOTINAMIDE 2-FLUOROADENINE DINUCLEOTIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE; SUGAR ACID;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; DRUG SYNTHESIS; FLUORINATION; PRODUCTIVITY; SIGNAL TRANSDUCTION; SILYLATION; STEREOCHEMISTRY; ANALOGS AND DERIVATIVES; CHEMISTRY; ENZYME SPECIFICITY; HALOGENATION; STEREOISOMERISM; SYNTHESIS;

HALOGENATION; LACTONES; NAD; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SUGAR ACIDS;

EID: 70349119913     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900637f     Document Type: Article

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