Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of <scp>d</scp>-Gulose, 6-Deoxy-<scp>d</scp>-gulose, <scp>l</scp>-Glucose, 6-Deoxy-<scp>l</scp>-glucose, and Related Sugars

Liu, Zilei; Yoshihara, Akihide; Jenkinson, Sarah F.; Wormald, Mark R.; Estévez, Ramón J.; Fleet, George W. J.; Izumori, Ken

doi:10.1021/acs.orglett.6b02041

Cited by 10 publications

(8 citation statements)

References 48 publications

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“…In 2016, Liu et al reported a multigram synthesis of L‐glucose from sodium D‐glucoheptonate 16 [27] . Sodium glucoheptanoate can be prepared via well‐known Killiani reaction using sodium cyanide and D‐glucose.…”

Section: Strategies For the Synthesis Of L‐sugarsmentioning

confidence: 99%

“…In 2016, Liu et al reported a multigram synthesis of Lglucose from sodium D-glucoheptonate 16. [27] Sodium glucoheptanoate can be prepared via well-known Killiani reaction using sodium cyanide and D-glucose. The work portrays the synthesis of a common intermediate 17 that gives access to Lglucose, L-glucoronic acid and L-glucitol (Scheme 3).…”

Section: Head To Tail Inversion Of D-hexosesmentioning

confidence: 99%

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Synthesis of L‐Hexoses: An Update

Paul

Kulkarni

2021

The Chemical Record

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Over the years, carbohydrates have increasingly become an important class of compounds contributing significantly to the target specific drug discovery and vaccine development. Several oligosaccharides contain L‐hexoses that are biologically relevant as therapeutic and diagnostic tools. Since, L‐hexoses and deoxy L‐hexoses are not readily available in large amount and pure form, attention is drawn towards development of cost effective and high yielding synthetic routes for their procurement. In this review we give an update on the recent developments in strategies for synthesis of L‐hexoses and deoxy L‐hexoses.

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Section: Strategies For the Synthesis Of L‐sugarsmentioning

confidence: 99%

Section: Head To Tail Inversion Of D-hexosesmentioning

confidence: 99%

Synthesis of L‐Hexoses: An Update

Paul

Kulkarni

2021

The Chemical Record

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“…As previously described, 12 the stable triflate 16, formed in 95% yield from 6, with sodium azide in DMF at -40 °C formed the kinetic glucono-azide 8 (75%) but at room temperature gave the thermodynamic mannonoazide 9 (85%); the initially formed 8 was equilibrated to the more stable all cis-azide 9. For the synthesis of the idono-and gulono-azides 10 and 11, the starting material 6-deoxy-Dgulonolactone 18 was prepared from the triacetonide 17 in 61% yield with no chromatography required; the route 13 is far more convenient than procedures from L-rhamnose 12 or Dgulonolactone (Scheme 3). 14 Reaction of 18 with benzaldehyde in the presence of concentrated hydrochloric acid gave the crystalline lactone 7 (92%) in which the methyl group is equatorial.…”

Section: Synthesis Of Azidolactones 8 9 10 and 11mentioning

confidence: 99%

Hanessian-Hullar reaction in the synthesis of highly substituted trans-3,4-dihydroxypyrrolidines: Rhamnulose iminosugar mimics inhibit α-glucosidase

et al. 2020

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“…Recently, Fleet, Yoshihara and coworkers (Liu et al, 2016 ) offered a very robust approach to some of the discussed compounds. The synthesis starts with easily available glucoheptanoic acid 19 ( Figure 7 ) with all the OH groups protected as acetonides.…”

Section: Bifunctional Monomers Equipped With Additional Reactive Moiementioning

confidence: 99%

Carbohydrate-Based Micro/Nanocapsules With Controlled External Surface for Medical Applications

Bielski

Witczak

Newport³

2020

Front. Chem.

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Micro/nanocapsules would have many more applications if we were able to controllably populate their surface with various chemical moieties. The present review introduces a novel variant of interfacial polymerization (IP) as a very robust method of manufacturing reservoir micro/nanocapsules equipped with several different functionalities on the capsules' surface. We call the method-IPCESCO (Interfacial Polymerization for Capsules' External Surface Control). As always in IP, the capsules' forming reaction is between monomers dissolved in opposite phases (oil or water) and takes place at the interface. Each monomer carries two or more functionalities reacting with functional groups of the monomer dissolved in the other phase. IPCESCO requires that one or both monomers are additionally equipped with (protected) functional groups interfering neither with the payload nor with the polymer formation. These additional groups end up everywhere in the polymeric shell but most importantly they are present on the external surface of capsules. These "handles" allow for the introduction of various moieties onto the capsules' surface. Since carbohydrate chemists developed a plurality of protecting and deprotecting methods for various functional groups such as aldehyde and hydroxyl, modified mono, and oligosaccharides are particularly well-suited to act as monomers in IPCESCO. The article discusses possible monomers and their synthesis, the transformation of protected reactive groups on the external capsules' surface into the desired functionalities, the control of the number of moieties on the surface and the capsules surface's architecture. The most important application of the novel encapsulation technology is in drug delivery. Possible surface units facilitating capsules' transport in the body, delivery to specific locations and mechanisms of capsules rupture are also addressed. Other applications of novel capsules include an ultra-sensitive quantitation and removal of pathogens, transport of nutrients in plants, detection of various antigens and other parameters in single cells.

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Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d-Gulose, 6-Deoxy-d-gulose, l-Glucose, 6-Deoxy-l-glucose, and Related Sugars

Cited by 10 publications

References 48 publications

Synthesis of L‐Hexoses: An Update

Synthesis of L‐Hexoses: An Update

Hanessian-Hullar reaction in the synthesis of highly substituted trans-3,4-dihydroxypyrrolidines: Rhamnulose iminosugar mimics inhibit α-glucosidase

Carbohydrate-Based Micro/Nanocapsules With Controlled External Surface for Medical Applications

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