Journal ArticleDOI
Direct preparation of 2-deoxy-d-glucopyranosides from glucals without ferrier rearrangement
TLDR
In this paper, an efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described.Abstract:
An efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is describedread more
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Journal ArticleDOI
Unusual behaviour of aryl 2-deoxy-D-galactosides under Lewis acid catalysis: a facile entry to C-aryl 2-deoxy-D-glycosides and bridged chiral benzopyran derivatives
TL;DR: In this article, the unusual behavior of aryl 2-deoxy-D-galactopyranosides yielding two different products with BF 3 ·Et 2 O under different concentrations was reported.
Journal ArticleDOI
Direct Addition of Amides to Glycals Enabled by Solvation-Insusceptible 2-Haloazolium Salt Catalysis.
TL;DR: This work shows the first direct 2-deoxyglycosylation of amide groups using a newly designed Brønsted acid catalyst under mild conditions, and discovers that the amide group can inhibit acid catalysts, and the inhibition has made the 2- deoxyglyCosylation reaction difficult.
Journal ArticleDOI
Reactivity switching and selective activation of C-1 or C-3 in 2,3-unsaturated thioglycosides.
TL;DR: Reactivity switching and selective activation of C-1 or C-3 in 2,3-unsaturated thioglycosides, namely, 2, 3-dideoxy-1-thio-D-hex-2-enopyranosides are reported, and glycals underwent glycosylation with alcohols to afford 3-ethylthio -2-deoxy glycosides.
Book ChapterDOI
Morphine alkaloids: History, biology, and synthesis.
TL;DR: A short overview of the history of morphine since it's isolation by Serturner in 1805 can be found in this paper, where the biosynthesis of the title alkaloid as well as all total and formal syntheses of morphine and codeine are discussed in detail.
Journal ArticleDOI
Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides
TL;DR: In this paper, the effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides was examined using substrates substituted only at selected positions.