Synthesis of 2'-deoxy-2'(s)-deuterio and 2'-deoxy-2'(r)-deuterio-β-D-nucleosides

Pathak, T. ; Bazin, H. ; Chattopadhyaya, J. (1986) Synthesis of 2'-deoxy-2'(s)-deuterio and 2'-deoxy-2'(r)-deuterio-β-D-nucleosides Tetrahedron, 42 (19). pp. 5427-5441. ISSN 0040-4020

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Lithium aluminium deuteride (LAD) promoted ring-opening reactions of appropriately protected methyl 2,3-anhydro-α-D-ribofuranoside 2 and methyl 2,3-anhydro-β-D-lyxofuranoside 10, gave 2-deoxy-2(S)-deuterio-erythro-pentose and 2-deoxy-2(Full-size image (R)-threo-pentose derivatives, 4a and 12a, respectively. Compounds 4a and 12a were subsequently converted to 2-deoxy-2(S)-deuterio- and 2-deoxy-2(R)-deuterio-erythro-pentofuranosyl chlorides, Full-size image (<1 K) and Full-size image (<1 K) respectively.Thymine, Cytosine, 6-chloropurine and 2-amino-6-chloropurine were then glycosylated with these α-chlorosugars, 8 and 17, to give the corresponding stereospecifically labelled 2-deoxy-2(S)-deuterio- and 2-deoxy-2(R)-deuterio-β-D-nucleosides.

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