Journal ArticleDOI
Dispiroketals in synthesis (part 2): A new group for the selective protection of diequatorial vicinal diols in carbohydrates.
TLDR
Dispiroketal formation as a new method for the selective protection of trans diequatorial vicinal diols in carbohydrate systems is reported in this article, where the authors show that it can be applied to a wide range of applications.About:
This article is published in Tetrahedron Letters.The article was published on 1992-08-11. It has received 48 citations till now. The article focuses on the topics: Protecting group & Vicinal.read more
Citations
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Journal ArticleDOI
1,2-diacetals: a new opportunity for organic synthesis.
Steven V. Ley,Daniel K. Baeschlin,Darren J. Dixon,Alison C. Foster,Stuart J. Ince,Henning W. M. Priepke,Dominic J. Reynolds +6 more
TL;DR: The use of 1,2-diacetals for a number of synthetic applications to provide diol protection and reactivity control was studied in this article, where the chiral versions of these systems were used to desymmetrize the enantiotopic diol pairs and to discriminate diequatorial diols in many carbohydrate derivatives.
Journal ArticleDOI
Butane 2,3-Bisacetal Protection of Vicinal Diequatorial Diols.
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De Novo Asymmetric Synthesis of the Anthrax Tetrasaccharide by a Palladium‐Catalyzed Glycosylation Reaction
Haibing Guo,George A. O'Doherty +1 more
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Synthesis of a 28-mer oligosaccharide core of Mycobacterial lipoarabinomannan (LAM) requires only two n-pentenyl orthoester progenitors
TL;DR: The 28-mer, 93 (MW = 11122.54) is, as far as the authors are aware of, the largest hetero-oligosaccharide that has been synthesized.
Journal ArticleDOI
A Solvation-Assisted Model for Estimating Anomeric Reactivity. Predicted versus Observed Trends in Hydrolysis of n-Pentenyl Glycosides1
TL;DR: In this article, an attempt has been made to predict qualitative trends in reactivity at the anomeric center, using N-bromosuccinimide-induced hydrolysis of n-pentenyl glycosides (NPGs) as the experimental model.
References
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Journal ArticleDOI
An efficient thioglycoside-mediated formation of α-glycosidic linkages promoted by iodonium dicollidine perchlorate
G. H. Veeneman,J. H. Van Boom +1 more
TL;DR: In this article, a specific glycosidation of partially-benzoylated thioglycosides with perbenzylated donors was demonstrated in the presence of the promotor iodonium dicollidine perchlorate.
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Kinetic acetalization for 1,2- and 1,3-diol protection by the reaction of p-methoxyphenylmethyl methyl ether with DDQ
TL;DR: When 1,2- and 1,3-diols were treated with PMME in the presence of DDQ, the kinetically controlled oxidative acetalization occurred smoothly even in case of acid-labile compounds to give p-methoxybenzylidene acetals rather stereoselectively as discussed by the authors.
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An Improvement in the Preparation of Some Carbohydrate Benzylidene Acetals
TL;DR: Carbohydrate benzylidene and p- methoxybenzylidsene acetals are easily prepared by treatment of various sugar derivatives with either benzaldehyde diethyl acetal or p-m methoxy-benzaldehyde diacetal, respectively, in refluxing chloroform containing camphorsulfonic acid as mentioned in this paper.
Journal ArticleDOI
Synthesis of a cell wall component of haemophilus (actinobacillus) pleuropneumoniae type 2
TL;DR: Coupling of properly protected repeating tetrasaccharide units of Haemophilus (Actinobacillus) pleuropneumoniae could be realized by regioselective phosphorylation.