Reaction of 2,3-unsaturated aryl glycosides with lewis acids : a convenient entry to C-aryl glycosides
TL;DR: In this article, a facile synthesis of 2,3-unsaturated aryl glycosides by BF 3.Et 2 O mediated O to C transformation was reported.
About: This article is published in Tetrahedron Letters.The article was published on 1992-05-19. It has received 22 citations till now. The article focuses on the topics: Aryl & Lewis acids and bases.
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TL;DR: In this paper, the Ferrier reaction of hindered phenols and alcohols was used to obtain α-2,3-unsaturated glucoside acetates in good yields and with good stereoselectivity.
16 citations
TL;DR: In this paper, a variety of alkenol tetrahydropyran derivatives were prepared and subjected to a tin tetrachloride promoted anomeric oxygen to carbon rearrangement.
Abstract: A variety of alkenol tetrahydropyran derivatives were prepared and subjected to a tin tetrachloride promoted anomeric oxygen to carbon rearrangement. Using this methodology many of the corresponding carbon-linked structures were synthesised, including alkenes and bicyclic ethers, in good yields. On the basis of an isotopic labelling study using 2H incorporated into the side chain and ring system it is proposed that these reactions proceed via an intermolecular pathway.
16 citations
TL;DR: In the course of this study, it was revealed that the Pseudomonas lipase-catalyzed acetylation occurred in a high yield exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.
Abstract: N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O-acetyl-D-glucal based on lipase-catalyzed selective protection of primary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacetimidates, and stereoselective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase-catalyzed acetylation occurred in a high yield (> 90%) exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.
14 citations
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.
11 citations
TL;DR: In this article, a remarkable difference was observed in the rates of [3,3]-sigmatropic rearrangement of aryl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides 1 and 2.
Abstract: A remarkable difference is observed in the rates of [3,3]-sigmatropic rearrangement of aryl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides 1 and 2; the slower reactivity of the alpha-isomers is consistent with AM1 calculated transition state energetics of model systems.
11 citations
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TL;DR: This chapter reviews recent advances in the chemistry and biochemistry of C-nucleosides, the literature concerning C-arylglycoside (i.e., nonnitrogen heterocyclic C- nucleoside) antibiotics, and recent significant advances in The most frequently used strategy for C-methine synthesis involves the construction of a heterocyClic aglycone from the C-1 substituent of a functionalized sugar intermediate.
Abstract: Publisher Summary This chapter reviews recent advances in the chemistry and biochemistry of C-nucleosides, the literature concerning C-arylglycoside (i.e., nonnitrogen heterocyclic C-nucleoside) antibiotics, and recent significant advances in the synthesis of C-nucleosides and C-glycosides. It also discusses biological test data and data that are relevant to structure–activity relationships. Modification of readily available natural C-nucleosides is an attractive route to new C-nucleoside analogs and derivatives, because one starting material often possesses much of the desired functionality and chiral properties. The chapter illustrates this approach with examples. The most frequently used strategy for C-nucleoside synthesis involves the construction of a heterocyclic aglycone from the C-1 substituent of a functionalized sugar intermediate.
179 citations
TL;DR: In this paper, Cp 2 HfCl 2 -AgClO 4 is particularly effective for this conversion, which leads to initial O-glycoside formation followed by rearrangement to C-congener.
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