Next Article in Journal
Synthesis, Structure and Hirshfeld Surface Analysis of Phosphine–Imidazolium Salt
Previous Article in Journal / Special Issue
Synthesis of (R) and (S)-3-Chloro-5-(2,4-dimethylpiperazin-1-yl)-4H-1,2,6-thiadiazin-4-ones
Open AccessFeature PaperShort Note

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

School of Chemistry, National University of Ireland, H91 TK33 Galway, Ireland
*
Author to whom correspondence should be addressed.
Molbank 2020, 2020(2), M1140; https://doi.org/10.3390/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.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop