Topic
Glucal
About: Glucal is a research topic. Over the lifetime, 590 publications have been published within this topic receiving 8960 citations. The topic is also known as: D-glucal.
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TL;DR: In this paper, N-Bromosuccinimide (1.1 eq) in the presence of potassium carbonate (2 eq) and a catalytic amount of dibenzoyl peroxide converts the allylic silyl ethers (O-TBDMS or O-SiEt3) of secondary allylic alcohols, derived from D-glucal 3a into corresponding dihydro γ-pyrones 2.
10 citations
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TL;DR: The total synthesis of polygalolide A, a secondary metabolite that was isolated from a Chinese medicinal plant, is reported and it is revealed that the combination of trimethylsilyl trifluoromethanesulfonate and 2,4,6-collidine successfully afforded the desired product as a single diastereomer.
Abstract: The total synthesis of polygalolide A, a secondary metabolite that was isolated from a Chinese medicinal plant, is reported. A key issue in this synthesis was construction of an oxabicyclo[3.2.1] skeleton, which was solved by the development of an intramolecular Ferrier-type C-glycosylation of a glucal with siloxyfuran as an internal nucleophile. The substrate was prepared from D-glucal by the introduction of trimethylsilylacetylene and siloxyfuran groups. Although C-glycosylation did not occur under the conditions found from model experiments, further examination revealed that the combination of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,4,6-collidine successfully afforded the desired product as a single diastereomer. The siloxy group at the C3 position played a crucial role in the stereocontrol of this reaction. The product was further transformed into a tetracyclic compound as follows: The vinyl ether and acetylenic moieties were reduced and the siloxy group was removed with a Barton–McCombie reaction. The construction of the six-membered ether and the γ-lactone provided the tetracyclic compound. Finally, a phenolic moiety was introduced by using a Mukaiyama aldol reaction to furnish polygalolide A.
10 citations
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TL;DR: Optically active threo-3-[(benzyloxycarbonyl)oxy]-2-fluorotetradecanoic acid, (2R,3S)-11, was synthesized from 3,4,6-tri-O-acetyl- D -glucal via methyl uronate derivative (5) as mentioned in this paper.
10 citations
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TL;DR: In this article, Ferrier glycosylation was used for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.
Abstract: Various acceptors including carbohydrates, amino acids, natural products, and hydroxylamine derivatives were coupled with 3,4,6-tri-O-acetyl- d -glucal in the presence of Cu(OTf)2 as catalyst. The protocol offers facile and efficient Ferrier glycosylation for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.
10 citations
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TL;DR: Synthese d'anhydro-1,5 desoxy-2 di-O-acetyl-3,4 O-tosyl-6 (ou Sacetyl -6) hexene-1 itol (ou thio-6 hexene 1 itol) a partir de D-glucose and de chlorure d'acide p-toluenesulfonique (ou de thioacetate de potassium) as discussed by the authors.
10 citations