Synthesis of 2′,3′-dideoxynucleosides via C-S bond cleavage: N-glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycoside

Tetrahedron Letters

Volumn 47, Issue 29, 2006, Pages 5147-5150

  Mitsudo, Koichi ^a   Matsuda, Wataru ^a   Miyahara, Seiji ^a   Tanaka, Hideo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; 2,3 DIDEOXY 1 [(2 PYRIDYLMETHYL)THIO]GLYCOSIDE; ALPHA THIODIDEOXYGLYCOSIDE; BETA THIODIDEOXYGLYCOSIDE; CARBON; GLYCOSIDE; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; GLYCOSYLATION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 33744995020     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.060     Document Type: Article

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17. The stereoisomers of 1a-c could be separated easily by silica gel column chromatography, and the pure isomers were used for the following reactions.
18. 4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/EtOAc 5:1 → 3:1 → 2:1 → 1:1) to afford 3a (29 mg, 80%, β/α = 5.2) as a colorless liquid (Table 3, entry 2).
19. 4.