Cyclit‐Reaktionen, XV. Synthese von Pseudodisacchariden mit Etherverknüpfung

Paulsen, Hans; Deyn, Wolfgang von

doi:10.1002/jlac.198719870207

Cited by 24 publications

(7 citation statements)

References 23 publications

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“…71 The displacement of the primary gluco triflate (233) by alkoxides derived from various carbasugar C-1 alcohols (225-227) took place in THF at rt, giving the ether-linked (1?6)Glc pseudodisaccharides (236-238) in excellent yield (Table 11, entries 1-3). 71 The alkoxides were generated from the alcohols and NaH, but KOtBu could also be used in combination with 18-crown-6.…”

Section: Triflate Displacementmentioning

confidence: 99%

“…Yields of pseudodisaccharide coupling products in THF were low, but adding DMF or HMPA as co-solvent gave better yields, and some ether-linked pseudodisaccharides (239-243) could be synthesised from the corresponding alcohols (225 and 228-231) by this method (Table 11, entries 4-8). 71,41 In my laboratory, we synthesised a pseudodisaccharide based on 3-substituted glucose (244) by coupling of a carbasugar C-1 alcohol (232) with an allo 3-triflate (235) ( Table 11, entry 9). 72 The yields for the synthesis of (1?6)-and (1?4)-linked compounds, at least, are high, and apparently independent of the structure of the nucleophile, from which we may infer that this approach may be used to synthesise other carbasugar pseudodisaccharides linked (1?4) or (1?6) to glucose.…”

Section: Triflate Displacementmentioning

confidence: 99%

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Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides

Cumpstey

2009

Carbohydrate Research

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Section: Triflate Displacementmentioning

confidence: 99%

Section: Triflate Displacementmentioning

confidence: 99%

Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides

Cumpstey

2009

Carbohydrate Research

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“…Aldehyde 5, [12] obtained from commercially available 2,3,4,6-tetra-O-benzyl--glucopyranose, was treated with [(ethoxycarbonyl)-and (benzyloxycarbonyl)methylene]triphenylphosphorane (Scheme 2) to afford the α,β-unsaturated esters 6 and 7. It is noteworthy that, in a combinatorial approach, the use of different stabilized ylides allows the introduction of different substituents at C (1).…”

Section: Formation Of the αβ-Unsaturated Ester And Michael Addition mentioning

confidence: 99%

Synthesis of Imino Sugar Scaffolds for the Generation of Glycosidase Inhibitor Libraries

et al. 2004

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We have synthesized imino sugar scaffolds bearing two points of diversity -the stereocenters located in α positions relative to the nitrogen atom -and three points of orthogonal derivatization -a carboxylic function, the primary hydroxy group, and the ring nitrogen atom. The key steps in the synthetic approach are the chain elongation of aldehyde 5 with the formation of an α,β-unsaturated ester, the Michael addition of an amine, and the final cyclization. This strategy leads to the preparation of different N-substituted imino

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“…The structure of 2 was confirmed by 1H NMR analysis in D20 at 300 MHz: 6 1.60-1.72 (m, 2H, 7-H), 1.74-1.84 (m, l H , 5-H), 3.57 (t, l H , J4,3 54. 5 9.8 Hz, 4-H), 3.61(dd, l H , J61,5 5.5,161, 6 11.3 Hz, 6'-H), 3.67 (dd, l H , J3,2 3.4 Hz, 3-H), 3.69 (dd,lH,J6,53.8H~,6-H),3.90(bt,lH,J2,13.2H~,2-H),3.98 (9, 1H, J1,7a J1,7e 3.2 Hz, 1-H)-It is noteworthy that none of the original chiral centres in quinic acid are retained in the target molecules. This feature indicates the degree of steric control which can be achieved at each transformation.…”

mentioning

confidence: 99%