Novel and efficient regioselective enzymatic approach to 3′-, 5′- and 3′,5′-di-O-crotonyl 2′-deoxynucleoside derivatives

Tetrahedron Letters

Volumn 46, Issue 35, 2005, Pages 5835-5838

  Díaz Rodríguez, Alba ^a   Fernández, Susana ^a   Lavandera, Iván ^a   Ferrero, Miguel ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXYNUCLEOSIDE; LIPASE B;

ACYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA; CATALYSIS; ENZYME SYNTHESIS; ISOMERIZATION;

BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA;

EID: 23044465985     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.138     Document Type: Article

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25. GC conditions: a capillary column TRACSIL TRB-5A (30 m × 0.32 mm × 0.50 μm) was used with nitrogen as carrier gas and a flame ionization detector. Injector and detector temperatures were set at 300°C, head column pressure at 13.1 psi and split 50:1; column initial temperature 220°C (3 min), rate 5°C/min until 260°C, then 15 min at 260°C, followed by heating rate 5°C/min until 300°C, column final temperature was 300°C (10 min). Samples (100 μL) were silylated as described in the literature (C.C. Sweeley, R. Bentley, M. Makita, and W.W. Wells J. Am. Chem. Soc. 85 1963 2497 2507 ). 3′,5′-di-O-TMS-thymidine appears at 12.3 min; 5′-O-crotonyl-3′-O-TMS-thymidine at 17.9 min; 3′-O-crotonyl- 5′-O-TMS-thymidine at 18.8 min; compound 4a at 29.7 min; 5′-O-but-3″-enoyl-3′-O-TMS-thymidine at 16.1 min; 3′-O-but-3″-enoyl-5′-O-TMS-thymidine at 17.2 min; 7 at 23.0 min; compounds 8 and 9 at 25.6 and 26.7 min
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