Rapid Access to 1,6-Anhydro-β-<scp>l</scp>-hexopyranose Derivatives via Domino Reaction: Synthesis of <scp>l</scp>-Allose and <scp>l</scp>-Glucose

D’Alonzo, Daniele; Guaragna, Annalisa; Napolitano, Carmela; Palumbo, Giovanni

doi:10.1021/jo800775v

Cited by 20 publications

(18 citation statements)

References 30 publications

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“…Herein, synthesis of enantiopure L ‐hexitol nucleoside monomers 13 and 14 (Scheme ) as building blocks for the preparation of L ‐HNA was carried out on the basis of a recently reported procedure17 already devoted to L ‐hexose synthesis 18. According to this strategy, construction of the 1,6‐anhydrosugar backbone 2 was achieved by a domino reaction19 by treating acetate 1 with DDQ (Scheme ). Such a reaction involves five formal synthetic transformations in one step: MPM group removal, oxidation of the resulting primary alcohol, acetonide removal and acetalation by double intramolecular cyclisation (89 %).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Base Pairing Properties of 1′,5′‐Anhydro‐L‐Hexitol Nucleic Acids (L‐HNA)

D’Alonzo¹,

Guaragna²,

Palumbo³

et al. 2009

Chemistry A European J

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Oligonucleotides composed of 1',5'-anhydro-arabino-hexitol nucleosides belonging to the L series (L-HNA) were prepared and preliminarily studied as a novel potential base-pairing system. Synthesis of enantiopure L-hexitol nucleotide monomers equipped with a 2'-(N(6)-benzoyladenin-9-yl) or a 2'-(thymin-1-yl) moiety was carried out by a de novo approach based on a domino reaction as key step. The L oligonucleotide analogues were evaluated in duplex formation with natural complements as well as with unnatural sugar-modified oligonucleotides. In many cases stable homo- and heterochiral associations were found. Besides T(m) measurements, detection of heterochiral complexes was unambiguously confirmed by LC-MS studies. Interestingly, circular dichroism measurements of the most stable duplexes suggested that L-HNA form left-handed helices with both D and L oligonucleotides.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Base Pairing Properties of 1′,5′‐Anhydro‐L‐Hexitol Nucleic Acids (L‐HNA)

D’Alonzo¹,

Guaragna²,

Palumbo³

et al. 2009

Chemistry A European J

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“…Guaragna and co‐workers developed a de novo synthetic strategy for all eight l ‐hexoses via unusual sulfur‐containing tricyclic dihydropyrans; the synthesis of allose and glucose are shown in Scheme . The key feature of this strategy is the design of three‐carbon homologating reagent A , which can undergo the sequence of addition to aldehydes or esters, domino oxidative cyclization to form tricyclic dihydropyran intermediate B (mediated by DDQ), and desulfurization to yield dihydropyran intermediates.…”

Section: De Novo Synthesis Of Monosaccharides Via Dihydropyran Intermmentioning

confidence: 99%

De Novo Synthesis of Mono‐ and Oligosaccharides via Dihydropyran Intermediates

Song

Wang

Tang

2017

Chemistry An Asian Journal

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The importance of carbohydrates is evident by their essential role in all living systems. Their syntheses have attracted attention from chemists for over a century. Most chemical syntheses in this area focus on the preparation of carbohydrates from naturally occurring monosaccharides. De novo chemical synthesis of carbohydrates from feedstock starting materials has emerged as a complementary method for the preparation of diverse mono- and oligosaccharides. In this review, the history of de novo carbohydrate synthesis is briefly discussed and particular attention is given to methods that address the formation of glycosidic bonds for potential de novo synthesis of oligosaccharides. Almost all methods of this kind involve the formation of dihydropyran intermediates. Recent progress in forming dihydropyrans by Achmatowicz rearrangement, hetero-Diels-Alder cycloaddition, ring-closing metathesis, and other methods is also elaborated.

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“…In 2008, D′Alonzo et al. reported a rapid access to 1,6‐anhydro‐β‐ l ‐hexopyranose derivatives through domino reactions . In their strategy, a bicyclic compound ( 30 ), which was obtained from 1,2‐bis‐thioenol ether ( 29 ) in six steps, was treated with Amberlyst 15 in chloroform at room temperature.…”

Section: Construction Of 16‐anhydrohexopyranoses (68‐dioxabicyclo[mentioning

confidence: 99%

The Construction of Anhydro Monosaccharides

Xie

Lin

et al. 2016

Asian J Org Chem

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Anhydro monosaccharide is as pecific and distinctive category of carbohydrates, which is found in many naturally deriveda nd artificial bioactive substrates. In the field of organic chemistry,s ome anhydro sugars can be used as common synthons to construct different carbohydrate structures. The development of efficient methodologies for the constructiono fv ariousa nhydro sugar fragments is very important in carbohydrate chemistry,w hich has attracted considerable attention in the past few years. This reviewm ainly covers the development of new synthetic methods since 2000 and gives an overview of the development in the formation of anhydro monosaccharide structures. It systematically summarizes all methodst oe stablish an intramolecular ether bridge in furanose and pyranose structures, which are the mostc ommonly used monosaccharide fragments in carbohydrate chemistry.

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Rapid Access to 1,6-Anhydro-β-l-hexopyranose Derivatives via Domino Reaction: Synthesis of l-Allose and l-Glucose

Cited by 20 publications

References 30 publications

Synthesis and Base Pairing Properties of 1′,5′‐Anhydro‐L‐Hexitol Nucleic Acids (L‐HNA)

Synthesis and Base Pairing Properties of 1′,5′‐Anhydro‐L‐Hexitol Nucleic Acids (L‐HNA)

De Novo Synthesis of Mono‐ and Oligosaccharides via Dihydropyran Intermediates

The Construction of Anhydro Monosaccharides

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