Enantio- and diastereoselective synthesis of 4'-α-substituted carbocyclic nucleosides

Tetrahedron Asymmetry

Volumn 9, Issue 6, 1998, Pages 911-914

  Kato, Keisuke ^a   Suzuki, Hisaki ^b   Tanaka, Hiromichi ^b   Miyasaka, Tadashi ^b  

^a TOHO UNIVERSITY   (Japan)

^b SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIRETROVIRUS AGENT; ARISTEROMYCIN; CARBOCYCLIC NUCLEOSIDE; CARBOVIR; CYCLOPENTENE DERIVATIVE; NATURAL PRODUCT; PURINE DERIVATIVE; SILANE DERIVATIVE;

ALKYLATION; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL BOND; DIASTEREOISOMER; DRUG POTENCY; DRUG SYNTHESIS; ENANTIOMER; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROLYSIS; PRIORITY JOURNAL; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

EID: 0032571593     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00065-2     Document Type: Article

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25. 3, (iv) pivaloyl chloride, (v) TBDPSCl, (vi) KOH, MeOH] with 2-amino-6-chloropurine, followed by desilylation afforded the β-isomer 15c (18%) accompanied by the α-isomer 18 (18%). The relative stereochemistry of 15c and 18 was determined by NOE experiments (Scheme 2). In the case of 15a and 15b, the similar results of NOE experiments with 15c were observed.
26. ++K)