Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

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ID: 35521
2016
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Abstract
The C8’-epimeric pyranosyl amino acid core 2 of amipurimycin was synthesized from D-glucose derived alcohol 3 in 13 steps and 14% overall yield. Thus, the Sharpless asymmetric epoxidation of allyl alcohol 7 followed by trimethyl borate mediated regio-selective oxirane ring opening with azide, afforded azido diol 10. The acid-catalyzed 1,2-acetonide ring opening in 10 concomitantly led to the formation of the pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 12. Functional group manipulation in 12 gave 21 that on stereoselective β-glycosylation afforded the pyranosyl thymine nucleoside 2 – a core of amipurimycin.
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markad2016synthesisbeilstein Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Markad, Pramod R.;Kumbhar, Navanath;Dhavale, Dilip D.;
Journal Beilstein journal of organic chemistry
Year 2016
DOI
DOI not found
URL
https://doi.org/10.3762/bjoc.12.165
Keywords Keywords not found

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