Volume 27, Issue 11
Heterocyclic Compounds
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ChemInform Abstract: A New Approach to the Synthesis of 4-Thio-1,2-dideoxyribose.

I. A. O'NEIL

I. A. O'NEIL

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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K. M. HAMILTON

K. M. HAMILTON

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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J. A. MILLER

J. A. MILLER

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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First published: March 12, 1996

Abstract

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ChemInform Abstract

The readily available triflate (I) can be converted via two routes to the key compound (VIIIa). The first route employs hexamethylditin (II) and affords the desired intermediate (III) together with the novel dimer (IV). The second route avoids the high cost of (II) and the formation of the undesired (IV). The formation of (VIIIa) from (VI) is found to be a general method for the preparation of modified 5- thiosugars. Finally, (VIIIa) is transferred to the nucleic acid synthon (XIII).

chemical structure image

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