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Synthesis of (R) and (S)-3-Chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones
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School of Chemistry, National University of Ireland, H91 TK33 Galway, Ireland
Author to whom correspondence should be addressed.
Molbank 2020, 2020(2), M1140;
Received: 8 April 2020 / Revised: 22 May 2020 / Accepted: 25 May 2020 / Published: 3 June 2020
(This article belongs to the Special Issue Heterocycle Reactions)
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring. View Full-Text
Keywords: glucose; tetrahydropyran; deprotection; cyclisation; functionalized scaffold glucose; tetrahydropyran; deprotection; cyclisation; functionalized scaffold
MDPI and ACS Style

Bennett, J.; Murphy, P.V. (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol. Molbank 2020, 2020, M1140.

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