Journal ArticleDOI
Preparation of various C-2 branched carbohydrates using intramolecular radical reactions.
TLDR
A new and efficient method for the facile synthesis of C-2 branched carbohydrates has been developed using an intramolecular radical cyclization fragmentation reaction and an unexpected furanoside was obtained from a tributyltin iodide-promoted rearrangement of the radical intermediate.About:
This article is published in Carbohydrate Research.The article was published on 2000-12-01. It has received 11 citations till now. The article focuses on the topics: Glycal & Trimethylsilyl.read more
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Journal ArticleDOI
Recent advances in the stereoselective synthesis of carbohydrate 2-C-analogs.
Jian Yin,Jian Yin,Torsten Linker +2 more
TL;DR: The two main strategies are based on ring-opening of 1,2-cyclopropanated carbohydrates by various reagents, as well as radical additions to glycals and further transformations, developed in the group, characterized by high stereoselectivities and good yields and give access to a broad variety of functionalized carbohydrate 2-C-analogs.
Journal ArticleDOI
Applications of 2-C-Formyl-Glycals in Organic Synthesis
TL;DR: Recent developments in the synthesis and applications of 2-C-formyl-glycals, the versatile chiral intermediates, are summarized in this review.
Journal ArticleDOI
Preparation and reactions of iodo sugars
Journal ArticleDOI
A neighboring group participation strategy: direct and highly diastereoselective synthesis of 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives
TL;DR: Treatment of methyl 2-C-formylmethyl-2-deoxy-β-D-glucopyranoside with H2SO4–HOAc–Ac2O gave 2-acetoxyl-4,5-bis(benzyloxy)-6-[(benZyloxy)methyl]hexahydrofuro[2,3-b]pyran derivatives in high yield with excellent diastereoselectivity.
Reference EntryDOI
Radicals and Carbohydrates
Inés Pérez-Martín,Ernesto Suárez +1 more
TL;DR: A review of the progress in the area of radicals in carbohydrate chemistry with special attention to new developments published during the past decade can be found in this article, where the major focus is on inter-and intramolecular carbon-carbon bond-forming radical reactions, with emphasis on the preparation of C-glycosides, C-ketosides, c-disaccharides, and branched-chain sugars.
References
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Journal ArticleDOI
Formation of CC Bonds by Addition of Free Radicals to Alkenes
TL;DR: In this article, the rate of addition of alkyl radicals to alkenes is controlled by steric and polar effects, and the stabilities of the educts and products are of only limited importance, since the transition states for these exothermic reactions occur very early on the reaction coordinate.
Journal ArticleDOI
Rate constants and Arrhenius parameters for the reactions of some carbon-centered radicals with tris(trimethylsilyl)silane
Journal ArticleDOI
Application of the Ibuka-Yamamoto reaction to a problem in stereochemical communication: a strategy for the stereospecific synthesis and stabilization of the triene substructure of rapamycin through sulfone substitution
Journal ArticleDOI
CHO vs. CH:CH2 competition in radical cyclizations: is the 5-hexenyl radical really supreme?
TL;DR: In this article, the cyclisation radicalaire d'un radical formyl-5 pentyle was used to donner un cyclohexanol semble etre preferee a la cyclisation of a radical hexene-5yle.
Journal ArticleDOI
Vilsmeier-haack reactoin of glycals-a short route to C-2-formyl glycals☆
TL;DR: A short and straightforward route has been accomplished for the synthesis of C-2-formyl glycals by a Vilsmeier-Haack reaction of glycals.
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