Journal ArticleDOI
Effect of a nucleophilic substituent on the stero-chemistry of the koenigs-knorr reaction. stereospecific, synthesis of some a and β-linked disaccharides of l-fucose
TLDR
For example, the authors showed that reaction of the same nucleophilic derivatives with 2,3,4-tri-O -acetyl-α- l -fucopyranosyl bromide generally led to corresponding β- l-linked disaccharides.About:
This article is published in Carbohydrate Research.The article was published on 1979-09-01. It has received 18 citations till now. The article focuses on the topics: Koenigs–Knorr reaction & Disaccharide.read more
Citations
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Journal ArticleDOI
Advances in Selective Chemical Syntheses of Complex Oligosaccharides
TL;DR: A wide variety of complex oligosaccharides has now been made accessible as a result of methodological improvements in the sphere of chemical synthesis, which can be used for the study of conformations and interactions with protein-receptor molecules.
Journal ArticleDOI
Fortschritte bei der selektiven chemischen Synthese komplexer Oligosaccharide
TL;DR: In this article, the Synthesemethoden erlautert, die zur selektiven Verknupfung von Sacchariden zu Oligosaccharide entwickelt wurden.
Book ChapterDOI
Chemistry and Biochemistry of d- and l-Fucose
TL;DR: This chapter discusses the various aspects of the chemistry of fucoses, especially the developments made in this field, and explains their metabolism and biochemistry while pointing out the possible biological functions and medical applications of fucaoses and their compounds.
Journal ArticleDOI
Bismuth(V)-Mediated Thioglycoside Activation†
Journal ArticleDOI
A facile formation of 2,5-anhydro sugars by ring contraction in methyl hexopyranoside 2-triflates under conditions of nucleophilic displacement
TL;DR: There is some precedent, in hexopyranoside 2-triflates, for the facile rearrangement that the four representatives here investigated have been found to undergo, and the synthesis of these triflating from L-fucose is described.
References
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Journal ArticleDOI
Results and Problems of O-Glycoside Synthesis
Günter Wulff,Gerbard Röhle +1 more
TL;DR: The present progress report surveys recent developments in the formation of O-glycosidic bonds starting from 1-halo sugars and from sugar 1,2-orthoesters.
Journal ArticleDOI
Zur Synthese von Tetraacetyl-hexosen mit freiem 2-Hydroxyl. Synthese einiger Disaccharide
TL;DR: In this article, a new einfache Synthese of 1.3.4.2-verknupfte Disaccharide und das α-Galaktosido-β-galaktsid-(1.1) werden synthetisiert.
Journal ArticleDOI
Studies on the Koenigs-Knorr reaction
TL;DR: Two α-D -linked disaccharides, 6-O -α-D-glucopyranosyl- D -galactose and 3-O-α- D-GLU-D −Galactose, were synthesized by reaction of 2- O -benzyl-3,4,6-tri-O − p -nitrobenzoyl-α(or β- D −glucophyranosy bromide with 1,2:3, 4-di- O −isopropyl
Journal ArticleDOI
Studies on the koenigs-knorr reaction : Part III. A stereoselective synthesis of 2-acetàmido-2-deoxy-6-O-α-L-fucopyranosyl-D-glucose
M. Dejter-Juszynski,H.M. Flowers +1 more
TL;DR: The Koenigs-Knorr reaction of the bromide with benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α- D -glucopyranoside gave an almost stereospecific condensation, as shown by removal of protecting groups, reduction of the product to the corresponding disaccharide alcohol, and analysis of its pertrimethylsilyl) ether by gas-liquid chromatography as discussed by the authors.
Journal ArticleDOI
Studies on the koenigs-knorr reaction : Part IV: The effect of participating groups on the stereochemistry of disaccharide formation
TL;DR: Partial benzylation of methyl α-L -fucopyranoside gave the 2,4-, and 3,4-dibenzyl ethers in the ratio of 3:2, and no 2,3-isomer could be detected in the reaction mixture.
Related Papers (5)
Studies on the Koenigs-Knorr reaction : Part II. Synthesis of an α-L-linked disaccharide from tri-O-benzyl-α-L-fucopyranosyl bromide
Studies on the koenigs-knorr reaction : Part III. A stereoselective synthesis of 2-acetàmido-2-deoxy-6-O-α-L-fucopyranosyl-D-glucose
M. Dejter-Juszynski,H.M. Flowers +1 more