Conversion of <scp>d</scp>-Glucals into <scp>l</scp>-Glycals and Mirror-Image Carbohydrates

Boulineau, Fabien P.; Wei, Alexander

doi:10.1021/ol036183m

Cited by 22 publications

(12 citation statements)

References 32 publications

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“…Treatment of the resulting epoxide with a catalytic amount of sodium methoxide (10 %) in methanol provided epoxide-opened product 13 as a single diastereomer. [21] The depicted stereochemistry of 13 was fully supported by extensive NMR studies. Dess-Martin oxidation [22] of 13 followed by l-selectride reduction of the resulting ketone provided endo-alcohol 14 as a single isomer in 68 % yield over two steps.…”

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confidence: 83%

Probing Multidrug‐Resistance and Protein–Ligand Interactions with Oxatricyclic Designed Ligands in HIV‐1 Protease Inhibitors

et al. 2010

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A healthier HAART: We report the design, synthesis, biological evaluation, and X‐ray crystallographic analysis of a new class of HIV‐1 protease inhibitors. Compound 4 proved to be an extremely potent inhibitor toward various multidrug‐resistant HIV‐1 variants, representing a near 10‐fold improvement over darunavir (DRV). Compound 4 also blocked protease dimerization with at least 10‐fold greater potency than DRV.

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confidence: 83%

Probing Multidrug‐Resistance and Protein–Ligand Interactions with Oxatricyclic Designed Ligands in HIV‐1 Protease Inhibitors

et al. 2010

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“…In the frame of a project devoted towards mirror-image oligosaccharides and glycoconjugates, synthesis of the unnatural enantiomer Htype II blood group determinant trisaccharide 237 (D-Fuc-( 1 2)-L-Gal-( 1 4)-L-GlcNAc--OMe) has been devised [109] (Scheme 32). Besides building block 225, the path involves the use of L-glycals 232 and 233, which were stereoselectively prepared from D-glucal 229 via pseudodesymmetrization of the C-glycoside intermediate 230 [110]. …”

Section: -Deoxypentenosidementioning

confidence: 99%

Recent Advances in Monosaccharide Synthesis: A Journey into L-Hexose World

D’Alonzo¹,

Guaragna²,

Palumbo

2009

COC

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Last years have witnessed enormous progresses in glycomic field, mainly as a consequence of the crucial role carbohydrates have shown in biological systems. While up to a few years ago attention was mainly focused on the use of easily available D-sugars, a recent interest has emerged around their L-enantiomers, as they have been found to be key components of several bioactive compounds, whether in the form of oligosaccharides, glycopeptides, terpene glycosides or other clinically useful agents. However, L-sugars (L-hexoses especially) are rather rare in nature and not easily accessi-ble from inexpensive sources. As demand for their synthesis in considerable amount and high purity is more and more pressing, intense efforts have been addressed to the development of new and general methodologies for their construction. This review covers the synthetic routes to L-hexoses, mainly those coming from the new century. Methodologies for monosaccharide assembly will comprise de novo approaches, based on carbon chain elongation, hetero Diels-Alder reaction, asymmetric dihydroxylation up to the most recent amino acid-catalyzed aldol addition – as well as D-sugar manipulation strategies, including epimerization by chemical or enzymatic methods. Application of such protocols for the construction of biologically relevant oligosaccharides and natural products will be also briefly mentioned

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“…The de novo approaches, including substrate‐controlled methods (such as carbon chain elongation) 12 and catalyst‐controlled methods (such as asymmetric dihydroxylation, 13 Diels Alder cycloadditions, 14 and stereoselective aldol additions 15 ), use simple molecules as starting material, while the chemical or enzymatic methods employ appropriate sugars as starting materials 16 . Based on chemical methods, sugar elaborations can be realized by external epimerization 17 and epoxidation 18 . Enzymatic methods, recognized as valuable catalysts for sugar synthesis, have become a vital addition to conventional sugar chemistry approaches 19, 20 …”

Section: Introductionmentioning

confidence: 99%

The mechanism of sugar produced from simple glycolaldehyde derivative at ambient conditions

Zhao

Wang

et al. 2021

Int J of Quantum Chemistry

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A benchmark of sugar produced from simple glycolaldehyde derivative has been achieved at ambient conditions (Science, 2004, 305, 1752), which is the most important step to produce life in nature. However, the mechanism has never been clearly understood. Here, we report a reaction mechanism which includes a two‐step synthesis of sugars by selective aldol reactions based on the density functional theory (DFT) calculations. Results show that the prochirality of attacking orientation of the enamine intermediate and steric effect in proton transfer is the main cause for stereochemical preference. This work provides the theoretical insight of sugar produced in glycolaldehyde procedure and may assist the improvement of catalyst design for this procedure.

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Conversion of d-Glucals into l-Glycals and Mirror-Image Carbohydrates

Abstract: [reaction: see text] L-Glycals can be prepared in seven steps from readily available D-glucals, enabling the facile construction of mirror-image carbohydrates such as the L-lactosamine derivative shown above.

Cited by 22 publications

References 32 publications

Probing Multidrug‐Resistance and Protein–Ligand Interactions with Oxatricyclic Designed Ligands in HIV‐1 Protease Inhibitors

Probing Multidrug‐Resistance and Protein–Ligand Interactions with Oxatricyclic Designed Ligands in HIV‐1 Protease Inhibitors

Recent Advances in Monosaccharide Synthesis: A Journey into L-Hexose World

The mechanism of sugar produced from simple glycolaldehyde derivative at ambient conditions

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