Access to oxetane-containing psico-nucleosides from 2-methyleneoxetanes: A role for neighboring group participation?

Journal of Organic Chemistry

Volumn 76, Issue 24, 2011, Pages 9962-9974

  Liang, Yanke ^a   Hnatiuk, Nathan ^a   Rowley, John M ^b   Whiting, Bryan T ^b   Coates, Geoffrey W ^b   Rablen, Paul R ^c   Morton, Martha ^a   Howell, Amy R ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b Department of Obstetrics Gynecology   (United States)

^c SWARTHMORE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CIS-2-BUTENE-1 ,4-DIOL; COMPUTATIONAL STUDIES; DIASTEREO-SELECTIVITY; GOOD YIELD; NATURAL PRODUCTS; NUCLEOBASES;

BUTENES; CARBONYLATION; STEREOSELECTIVITY;

BIOMOLECULES;

1,4 BIS(BENZOYLOXY)BUT 2 ENE; 1,4 BIS(TERT BUTYLDIMETHYLSILYLOXY)BUT 2 ENE; 2,3 BIS(BENZOYLOXYMETHYL)OXIRANE; 2,3 BIS(TERT BUTYLDIMETHYLSILYLOXYMETHYL)OXIRANE; 2ALPHA(6 AMINO 7H PURIN 7 YL) 2ALPHA FLUOROMETHYL 3ALPHA,4ALPHA BIS(HYDROXYMETHYL)OXETANE; 2BETA(6 AMINO 9H PURIN 9 YL) 2ALPHA FLUOROMETHYL 3ALPHA,4BETA BIS(HYDROXYMETHYL)OXETANE; 3 (BENZOYLOXYMETHYL)DIHYDROFURAN 2(3H)ONE; 3 BENZOYLOXYMETHYL 2 METHYLENETETRAHYDROFURAN; 3 BENZOYLOXYMETHYL 4 (TERT BUTYLDIMETHYLSILYLOXYMETHYL) OXETAN 2 ONE; 3 BENZOYLOXYMETHYL 4 TERT BUTYLDIMETHYLSILYLOXYMETHYL 2 METHYLENEOXETANE; 3 BENZYLOXYMETHYL 4 (TERT BUTYLDIMETHYLSILYLOXYMETHYL) OXETAN 2 ONE; 3 BENZYLOXYMETHYL 4 HYDROXYDIHYDROFURAN 2(3H)ONE; 3,4 BIS(BENZOYLOXYMETHYL) 2 METHYLENEOXETANE; 3,4 BIS(BENZOYLOXYMETHYL)OXETAN 2 ONE; 3,4 BIS(TERT BUTYLDIMETHYLSILYLOXYMETHYL) 2 METHYLE NEOXETANE; 3,4 BIS(TERT BUTYLDIMETHYLSILYLOXYMETHYL)OXETAN 2 ONE; 3ALPHA,4BETA BIS(TERT BUTYLDIMETHYLSILYLOXYMETHYL) 2 (6 CHLORO 9H PURIN 9 YL) 2 FLUOROMETHYLOXETANE; 3ALPHA,4BETA BIS(TERTBUTYLDIMETHYLSILYLOXYMETHYL) 2 (6 CHLORO 7H PURIN 7 YL) 2 FLUOROMETHYLOXETANE; 4 BENZOYLOXY 3 (BENZOYLOXYMETHYL)DIHYDROFURAN 2(3H)ONE; 4 BENZOYLOXYDIHYDROFURAN 2(3H)ONE; 4 BENZOYLOXYMETHYL 3 (TERT BUTYLDIMETHYLSILYLOXYMETHYL)OXETAN 2 ONE; 4 BENZOYLOXYMETHYL 3 TERT BUTYLDIMETHYLSILYLOXYMETHYL 2 METHYLENEOXETANE; 4 BENZYLOXYMETHYL 3 (TERT BUTYLDIMETHYLSILYLOXYMETHYL)OXETAN 2 ONE; DIETHYL ERYTHRO 2 BENZYLOXYMETHYL 3 HYDROXYSUCCINATE; ETHYL ERYTHRO 2 BENZYLOXYMETHYL 3,4 DIHYDROXYBUTANOATE; FLUORINE; NUCLEIC ACID BASE; NUCLEOSIDE; OXETANE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBONYLATION; DEPROTECTION REACTION; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; HYDROGENOLYSIS; NUCLEIC ACID BASE SUBSTITUTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY;

ADENINE; ANTIVIRAL AGENTS; BUTYLENE GLYCOLS; EPOXY COMPOUNDS; ETHERS, CYCLIC; FLUORINE; FURANS; HUMANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEOSIDES; STEREOISOMERISM;

EID: 84055193866     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201565h     Document Type: Article

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