A General Synthesis of Cyclitols and Aminocyclitols from Carbohydrates

Semeria, D.; Maury, Philippe; Delaumény, Jeanne-Marie; Sepulchre, Anne‐Marie; Géro, S. D.

doi:10.1055/s-1983-30478

Cited by 77 publications

(27 citation statements)

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“…Closely following the discovery, by Umezawa, Takeuchi and colleagues, of cyclophellitol ( 1 ) and its annotation as a mechanism‐based retaining β‐glucosidase inhibitor, Tatsuta and co‐workers disclosed the first synthesis of cyclophellitol ( 1 ) and cyclophellitol‐aziridine ( 2 ), as well as their configurational analogues 1,6‐ epi ‐cyclophellitol ( 14 , Scheme ) and 1,6‐ epi ‐cyclophellitol‐aziridine 12 (atom numbering as indicated in Figure , compound 1 ). As with most literature syntheses of cyclophellitol, the Tatsuta scheme starts from a chiral building block, here partially protected d ‐idopyranose derivative 4 , which is prepared from l ‐glucose following established procedures . Swern oxidation and Wittig olefination on the primary alcohol is followed by hydrolysis of the methyl acetal.…”

Section: Synthetic Strategiesmentioning

confidence: 99%

The Synthesis of Cyclophellitol‐Aziridine and Its Configurational and Functional Isomers

et al. 2016

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Cyclophellitol and cyclophellitol-aziridine are potent, mechanism-based and irreversible retaining -glucosidase inhibitors. We have become interested in these configurationalglucoside analogues as they proved to be a highly suitable starting point for the development of activity-based glycosidase probes. In this review, we provide an overview of the cyclophellitol-aziridine synthesis reported in the literature. Two con-

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Section: Synthetic Strategiesmentioning

confidence: 99%

The Synthesis of Cyclophellitol‐Aziridine and Its Configurational and Functional Isomers

et al. 2016

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“…Thermolysiso fd ifluorosulfoxides 7 was achieved using Bn 3 Ni n Ph 2 Oa t1 90 8Cu nder air for 120 ht og ive the difluoroalkene 8 in 36 %y ield. An alternative route to alkene 8 was also explored starting from knownalkene 9 synthesized from 3.Hexoglucal 9 [31] was converted into lactone 10 by ozonolysis, [32] and 10 was converted into 8 using aW ittig olefination. However, this last step appeared to be rather delicate to implement.…”

Section: Introductionmentioning

confidence: 99%

Conformational Plasticity in Glycomimetics: Fluorocarbamethyl‐L‐idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings

Unione

Díaz

et al. 2015

Chemistry A European J

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Sugar function, structure and dynamics are intricately correlated. Ring flexibility is intrinsically related to biological activity; actually plasticity in L-iduronic rings modulates their interactions with biological receptors. However, the access to the experimental values of the energy barriers and free-energy difference for conformer interconversion in water solution has been elusive. Here, a new generation of fluorine-containing glycomimetics is presented. We have applied a combination of organic synthesis, NMR spectroscopy and computational methods to investigate the conformational behaviour of idose- and glucose-like rings. We have used low-temperature NMR spectroscopic experiments to slow down the conformational exchange of the idose-like rings. Under these conditions, the exchange rate becomes slow in the (19) F NMR spectroscopic chemical shift timescale and allows shedding light on the thermodynamic and kinetic features of the equilibrium. Despite the minimal structural differences between these compounds, a remarkable difference in their dynamic behaviour indeed occurs. The importance of introducing fluorine atoms in these sugars mimics is also highlighted. Only the use of (19) F NMR spectroscopic experiments has permitted the unveiling of key features of the conformational equilibrium that would have otherwise remained unobserved.

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“…[29] In subsequent papers, the enantiospecific synthesis of (ϩ)-1,6-epi-cyclophellitol (2) [7] and analogues 12 and 13 [30,31] (Figure 2) were also described by this group. [29] In subsequent papers, the enantiospecific synthesis of (ϩ)-1,6-epi-cyclophellitol (2) [7] and analogues 12 and 13 [30,31] (Figure 2) were also described by this group.…”

Section: Chemistry Of (؉)-Cyclophellitol (A) Synthesis Of Enantiomerimentioning

confidence: 95%

Cyclohexane Epoxides − Chemistry and Biochemistry of (+)-Cyclophellitol

Marco‐Contelles

2001

Eur. J. Org. Chem.

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This account reviews the biochemistry and chemistry of cyclophellitol (1). Particular emphasis is given to the different synthetic approaches described for cyclophellitol and related [a] working with Professor B. Fraser-Reid (free-radical chemistry; annulated sugars; formal total synthesis of phyllanthocin) (1988Ϫ1989). In 1986 he was appointed as Associate Researcher, and in 1992 he was promoted to Research Scientist in the CSIC. His present interests include the development of new synthetic methodologies in free-radical chemistry, carbohydrate chemistry, and PausonϪKhand reactions in sugar templates. He is also very active in asymmetric synthesis (Michael reaction) and biological evaluation of heterocyclic systems (CSIC reaction, tacrine analogues, and 2-amino-4Hpyrans). He was visiting Professor at the Université Pierre et Marie Curie, Paris VI (June 2000).MICROREVIEWS: This feature introduces the readers to the authors' research through a concise overview of the selected topic. Reference to important work from others in the field is included.

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A General Synthesis of Cyclitols and Aminocyclitols from Carbohydrates

Cited by 77 publications

References 0 publications

The Synthesis of Cyclophellitol‐Aziridine and Its Configurational and Functional Isomers

The Synthesis of Cyclophellitol‐Aziridine and Its Configurational and Functional Isomers

Conformational Plasticity in Glycomimetics: Fluorocarbamethyl‐L‐idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings

Cyclohexane Epoxides − Chemistry and Biochemistry of (+)-Cyclophellitol

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