Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of 2'-Deoxy-2'-thio-3'-deoxy-3'-aminouridine.
関谷 剛男浮田 忠之進
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1967 年 15 巻 10 号 p. 1503-1507

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A complex neighboring approach provided a successful synthesis of 2'-deoxy-2'-thio-3'-deoxy-3'-aminouridine (IX). 1-(3'-Deoxy-3'-amino-β-D-arabinofuranosyl) uracil (I) afforded, in three steps, the blocked dithiocarbamoyl mesylate (IV), which, on heating in pyridine, cyclized to the thiazoline (V), that was deblocked to VI and reduced to the thiazolidine (VII). Compound (VII) was successively treated with mercuric chloride and hydrogen sulfide to furnish the desired product (IX).

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