1,6-Anhydro Derivatives of Aldohexoses

Černý, M.; Staněk, Jan

doi:10.1016/s0065-2318(08)60324-8

Cited by 159 publications

(7 citation statements)

References 601 publications

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“…This is one of the very rare examples17 in which the violation of the Fürst–Plattner rules is reported for a carbon nucleophile in the field of 1,6‐anhydrosugars. Reports in the literature state that “hard” nucleophiles strictly open in a trans ‐diaxial manner, whereas “soft” ones occasionally open equatorially 14,15. Since the Normant cuprates are more on the “soft” side, our surprising result is in line with this explanation.…”

Section: Resultsmentioning

confidence: 99%

New Chiral Building Blocks and Branched 1,6‐Anhydro Sugars from Regio‐ and Stereoisomeric Černý Epoxides

2005

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Keywords: 1,6-Anhydro sugars / Chiral building blocks / Branched sugars / Č erný epoxides / Gilman cuprates / Epoxide rearrangement / Vinyl tosylate cross couplingThe tandem epoxideǞallyl alcohol rearrangement-cuprate cross-coupling previously described for the Č erný epoxide 1, to yield the allyl alcohol 2, was extended to the regioisomeric epoxy-tosylate 3, to yield allyl alcohol 4, and to the stereoisomeric epoxide 5 to afford the allyl alcohols of type 6. Further transformation of the products from this new two-step one-

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Section: Resultsmentioning

confidence: 99%

New Chiral Building Blocks and Branched 1,6‐Anhydro Sugars from Regio‐ and Stereoisomeric Černý Epoxides

2005

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“…The 1,6‐anhydrosugars levoglucosan (1,6‐anhydro‐β‐D‐glucopyranose) and cellobiosan (1,6‐anhydro‐β‐cellobiose) are products of thermal degradation processes (Černý and Staněk, ; Gao et al ., ; Dai, ). Two backgrounds: hot alkaline solutions (65°C–115°C) and high temperature (200°C–500°C), are typically responsible for the formation of the 1,6‐anhydro bond of sugars (Fig.…”

Section: 6‐anhydro Bond: a Cmb‐like Analoguementioning

confidence: 99%

“…Intriguingly, a glucosyltransferase was found in fungi, which makes levoglucosan as a by‐product when catalyzing the disaccharide maltose to synthesize oligosaccharides (Pazur et al ., ). As levoglucosan is also formed by pyrolysis of maltose (Černý and Staněk, ), the secondary reaction of the glucosyltransferase notably parallels the thermochemical processes. Nevertheless, the isolation of levoglucosan from fungal cells has not yet been reported.…”

Section: 6‐anhydro Bond: Continues In Eukaryotesmentioning

confidence: 99%

New insights into a hot environment for early life

Dai¹

2017

Environ Microbiol Rep

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Investigating the physical-chemical setting of early life is a challenging task. In this contribution, the author attempted to introduce a provocative concept from cosmology - cosmic microwave background (CMB), which is the residual thermal radiation from a hot early Universe - to the field. For this purpose, the author revisited a recently deduced biomarker, the 1,6-anhydro bond of sugars in bacteria. In vitro, the 1,6-anhydro bond of sugars reflects and captures residual thermal radiation in thermochemical processes and therefore is somewhat analogous to CMB. In vivo, the formation process of the 1,6-anhydro bond of sugars on the peptidoglycan of prokaryotic cell wall is parallel to in vitro processes, suggesting that the 1,6-anhydro bond is an ideal CMB-like analogue that suggests a hot setting for early life. The CMB-like 1,6-anhydro bond is involved in the life cycle of viruses and the metabolism of eukaryotes, underlying this notion. From a novel perspective, the application of the concept of the CMB to microbial ecology may give new insights into a hot environment, such as hydrothermal vents, supporting early life and providing hypotheses to test in molecular palaeontology.

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“…145 55 derivatives developed by Č erný and Stanek occupy an important niche. 155 First reported in the 1970s, Č erný epoxides, [156][157][158][159] for example, 65 (Scheme 13), have served as useful synthons for the synthesis of many biologically important derivatives. It was demonstrated that the ring opening of 65 with NaN 3 could be readily achieved in 9:1 DMF-water at 120°C to afford 66 in high yield of 80%.…”

Section: From O-sulfonyl Derivativesmentioning

confidence: 99%