The Transformation Mechanism of 3,4,6-Tri-O-acetyl-1,5-anhydro-2-deoxy-<scp>d</scp>-arabino-hex-1-enitol in Water

Madaj, Janusz; Rak, Janusz; Sokolowski, J.S.; Wiśniewski, Andrzej

doi:10.1021/jo950917u

Cited by 12 publications

(6 citation statements)

References 27 publications

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“…179 Mishra et al reported a water promoted, catalyst-free synthesis of 3-mercapto-or 3-dithiocarbamoyl-2-deoxycarbohydrate derivatives by the conjugate addition of thiols or dithiocarbamates to glycalderived a,b-unsaturated carbonyl compounds (Scheme 15). [180][181][182] Ziyaei-Halimehjani et al have described a water-promoted catalyst-free Michael addition of thioacetic and thiobenzoic acids to activated olefins. 183 3.1.2.…”

Section: Addition Reactionsmentioning

confidence: 99%

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

et al. 2013

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Catalyst-free reactions developed during the last decade and the latest developments in this emerging field are summarized with a focus on catalyst-free reactions in-water and on-water. Various named reactions, multi-component reactions and the synthesis of heterocyclic compounds are discussed including the use of various energy input systems such as microwave- and ultrasound irradiation, among others. Organic chemists and the practitioners of this art both in academia and industry hopefully will continue to design benign methodologies for organic synthesis in aqueous media under catalyst-free conditions by using alternative energy inputs based on fundamental principles.

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Section: Addition Reactionsmentioning

confidence: 99%

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

et al. 2013

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“…This would cause elimination of the leaving group at C-3, which itself is being instantaneously substituted by a molecule of water to form the hemiacetal, which then equilibrates with the open-chain a,b-unsaturated (Z) aldehyde that ultimately isomerizes to the more stable (E) enal. 12 Accordingly for acting at the olefinic bond we decided to use either CdI 2 or ZnI 2 (Zn, Cd and Hg belong to the same group). Both of these showed almost identical results, but our choice fell upon ZnI 2 which is nontoxic 9d and dissociates in water or polar organic solvents to a greater extent to furnish Zn 2+ and I À ions.…”

mentioning

confidence: 99%

An efficient synthesis of 2,3-dideoxy-α,β-unsaturated carbohydrate enals by mixed Lewis acid (HfCl4 and ZnI2) catalyzed hydration of glycals

Saquib

Sagar

Shaw

2006

Carbohydrate Research

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“…The substances found to be responsible for this activity were provisionally termed "prostaglandins" due to the belief that they were produced in the prostate gland. In actual fact, it has been shown that prostaglandins (PGs) are, in general, produced from arachidonic acid (56) close to the site where they are to exert a tissue-specific effect, whereupon they are rapidly metabolised to less active materials. 22…”

Section: Discovery Of Prostaglandinsmentioning

confidence: 99%

A Palladium-Catalysed Allylic Alkylation Cascade: Towards the Total Synthesis of Thromboxanes A₂ and B₂

Turner¹

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The design and development of new chemical reactions is crucial to the ongoing success of organic synthesis research. In this work the scope and utility of a recently discovered regioselective palladium-catalysed allylic alkylation (Pd-AA) cascade was explored through increasing the range of non-symmetric pyran-based biselectrophiles and β-dicarbonyl bis-nucleophiles that can be used in this reaction. Four differentially protected tri-substituted dihydropyrans based on glucose were synthesised, including 2,3-unsaturated silyl glycosides and α,β-unsaturated lactones. These substrates were assessed as bis-electrophiles in the Pd-AA cascade. One silyl glycoside bis-electrophile, possessing a carbonate leaving group, was shown to be an excellent substrate for reaction with a number of cyclic bis-nucleophiles. Furthermore, a series of regioisomeric methylated 4-hydroxycoumarins were synthesised, tested and found to be equally effective as bis-nucleophiles in the Pd-AA cascade with both acyclic and cyclic bis-electrophiles. Advances made during this research include a novel Ferrier reaction with silanol nucleophiles, which was found to produce silyl glycosides, albeit in low yields. Additionally, several Perlin aldehydes were generated by the Ferrier-type hydrolysis of 3,4,6-tri-O-acetyl-D-glucal and led to the discovery of discrepant structural assignments in the literature. Furthermore, a ¹³C NMR shielding template was generated as a tool for the stereochemical assignment of tri-substituted dihydropyrans. An extended variant of the Pd-AA cascade was achieved by employment of the bisnucleophile Meldrum’s acid with the optimal tri-substituted bis-electrophile in the presence of H₂O. The reaction afforded a γ-butyrolactone that could serve as a potential intermediate en route to the synthesis of the biologically interesting compounds thromboxanes A₂ and B₂. This extended Pd-AA cascade, although currently unoptimised, is capable of performing five synthetic transformations in one-pot and holds the potential to improve on the current syntheses of the thromboxanes.

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The Transformation Mechanism of 3,4,6-Tri-O-acetyl-1,5-anhydro-2-deoxy-d-arabino-hex-1-enitol in Water

Cited by 12 publications

References 27 publications

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

An efficient synthesis of 2,3-dideoxy-α,β-unsaturated carbohydrate enals by mixed Lewis acid (HfCl4 and ZnI2) catalyzed hydration of glycals

A Palladium-Catalysed Allylic Alkylation Cascade: Towards the Total Synthesis of Thromboxanes A₂ and B₂

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