537. 3 : 6–3′ : 6′-Dianhydro-derivatives of β-methylcellobioside and of β-methylmaltoside

Newth, F. H.; Nicholas, Sumesh; Smith, F.; Wiggins, L. F.

doi:10.1039/jr9490002550

Cited by 18 publications

(5 citation statements)

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“…Several β(1→4)- and β(1→3)-disaccharides were also used as acceptors. Methyl β-cellobioside 5 , methyl 6-bromo-6-deoxy-β-cellobioside 6 , N- acetyl-chitobiose 7 , and benzyl β-laminaribioside 8 gave the expected tetrasaccharides 12 − 15 in excellent yields (Table ) . Only N , N II -diacetyl-chitobiose, a close analogue of 7 with an additional acetyl group which should fit in +1 subsite, was found to be unable to act as an acceptor molecule.…”

Section: Resultsmentioning

confidence: 99%

Highly Efficient Synthesis of β(1 → 4)-Oligo- and -Polysaccharides Using a Mutant Cellulase

et al. 2000

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This report describes an efficient chemoenzymatic synthesis of a variety of regioselectively modified β(1→4)-oligo- and -polysaccharides. This successful approach was based on: (i) the use of a “glycosynthase” which is a Glu-197-Ala nucleophile mutant of the retaining cellulase endoglucanase I (Cel7B) from Humicola insolens and (ii) the rational design of modified acceptor and donor molecules through a careful examination of information given by the X-ray structures of wild type and mutated enzymes. The mutant was able to catalyze, in high yield, the regio- and stereoselective glycosylation of α-glycobiosyl fluorides both unsubstituted and modified with various mono- and disaccharide acceptors, as well as the polymerization of these donors through a single-step inverting mechanism.

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Section: Resultsmentioning

confidence: 99%

Highly Efficient Synthesis of β(1 → 4)-Oligo- and -Polysaccharides Using a Mutant Cellulase

et al. 2000

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“…This group could also strongly inhibit transportation by the ABC maltose transport system. The synthesis of target molecules 18a,b (Scheme 2) was performed via methyl maltoside 19, [21] its benzylidene derivative 20, [22] and the benzylation product 21, [23] which was transformed into the 4b-O-unprotected maltoside 22 [24] following literature procedures. Alkylation of 22 with 8-(triisopropylsilyloxy)-3,6-dioxa-octyl bromide (23) with sodium hydride as base in the presence of tetrabutylammonium iodide (TBAI) as promoter in DMF afforded compound 24.…”

Section: Modifications Of Maltosementioning

confidence: 99%

Maltose and Maltotriose Derivatives as Potential Inhibitors of the Maltose‐Binding Protein

2008

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Inhibition of substrate binding to maltose-binding protein (MBP) was investigated with structurally modified maltose and maltotriose derivatives that were designed based on the X-ray analysis of maltose and maltotriose bound to MBP. In maltose, positions 1a, 2a, 2b, 4b and 6b were modified (compounds 1-3, 18a, b, 28a-c, 39 and 44) of which only the trivalent maltose derivatives 39 and 44 exhibited high affinity to MBP. Maltotriose modifications were carried out at posi-

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“…Numerous procedures could be found in which Knoevenagel condensations were performed on the most diverse substrates employing different amines as catalysts (primary, secondary, tertiary or ammonium salts) [30,32] …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Regarding the nitrile derivatives of OBMF, only two scientific works can be found in the literature [30–31] . The first involved the dehydration of the aldoxime derivative of OBMF in acetic anhydride resulting in the desired product with a yield of 72 % after extraction in a chlorinated solvent [30] . In the other procedure OBMF was dissolved at room temperature in a tetrahydrofuran/ammonia solution; thus, molecular iodine was added, and the mixture was left to react for three days.…”

Section: Introductionmentioning

confidence: 99%

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Nitrile Furanics via Copper‐Catalyzed Dehydration of Aldoximes and Knoevenagel Condensation

Annatelli,

Sadraoui,

Trapasso

et al. 2024

Eur J Org Chem

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In this work two synthetic approaches to introduce nitrile moieties into bio‐based derived furanic compounds were investigated, i.e., dehydration of aldoximes and Knoevenagel condensation. Both methodologies have been first tested and optimized on furfural and thus exploited on 5‐hydroxymethyl‐2‐furfural (HMF) and 5,5’‐oxy(bismethylene)‐2‐furaldehyde (OBMF). The syntheses of furfural, HMF and OBMF aldoximes were efficiently conducted (also in large scale) under mild reaction conditions and short reaction time. The subsequent dehydration to nitrile furanic compounds was carried out in the presence of catalytic amount of copper acetate monohydrate. Furthermore, Knoevenagel condensations were performed on furfural, HMF and OBMF with different Activated Methylene Group compounds, using for the first‐time dimethyl carbonate as the reaction media. Most of the resulting products were isolated as pure via simple liquid‐liquid extraction in good to excellent yields. Future applications of these compounds might include aldoxime reduction into amine furanics ‐ herein also preliminary investigated ‐ and hydrolysis of the nitrile derivatives in the related carboxylic acid (or ester) furanics. All these products are interesting monomers for the preparation of bio‐based polymers.

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537. 3 : 6–3′ : 6′-Dianhydro-derivatives of β-methylcellobioside and of β-methylmaltoside

Cited by 18 publications

References 0 publications

Highly Efficient Synthesis of β(1 → 4)-Oligo- and -Polysaccharides Using a Mutant Cellulase

Highly Efficient Synthesis of β(1 → 4)-Oligo- and -Polysaccharides Using a Mutant Cellulase

Maltose and Maltotriose Derivatives as Potential Inhibitors of the Maltose‐Binding Protein

Nitrile Furanics via Copper‐Catalyzed Dehydration of Aldoximes and Knoevenagel Condensation

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