Synthetic studies toward pyruvate acetal containing saccharides. Synthesis of the carbohydrate part of the Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens

Ziegler, Thomas; Eckhardt, Elisabeth; Birault, Véronique

doi:10.1021/jo00057a021

Cited by 32 publications

(18 citation statements)

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“…201 1-Azaallylic anions were applied in the synthesis of (-)-malyngolide and (+)-epi-malyngolide, two naturally occurring compounds of the marine algae Lynbya majuscula, which display antibiotic activity. 202 The key step in the synthesis of (-)-(S,R)-malyngolide was the [3,3]sigmatropic rearrangement of allyloxycarbonylcyclopentanone RAMP-hydrazone (R)-655 after treatment with an excess of lithium tetramethylpiperidide (Scheme 132). Further elaboration in five steps led to the natural product 658 with 96% ee and 10% overall yield.…”

Section: Synthesis Of Pyrroles Pyrrolines and Pyrrol-2-onesmentioning

confidence: 99%

1-Azaallylic Anions in Heterocyclic Chemistry

2004

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Section: Synthesis Of Pyrroles Pyrrolines and Pyrrol-2-onesmentioning

confidence: 99%

1-Azaallylic Anions in Heterocyclic Chemistry

2004

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“…63 The selective activation of trichloroacetimidates over other glycosyl donors can be straightforwardly executed with TMSOTf 64 or BF 3 -OEt 2 . 65 For example, as a part of the synthesis of glycolipid of Mycobacterium smegmatis, TMSOTf-promoted coupling of trichloroacetimidate 49 and thioglycoside acceptor 50 afforded β(1→4) linked trisaccharide 51 in 71% yield (Scheme 13a).…”

Section: Selective Activationmentioning

confidence: 99%

“…65 For example, as a part of the synthesis of glycolipid of Mycobacterium smegmatis, TMSOTf-promoted coupling of trichloroacetimidate 49 and thioglycoside acceptor 50 afforded β(1→4) linked trisaccharide 51 in 71% yield (Scheme 13a). 64 …”

Section: Selective Activationmentioning

confidence: 99%

Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation

Kaeothip

Demchenko

2011

Carbohydrate Research

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Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. Oligosaccharide synthesis by selective activation of one leaving group over another is one such expeditious strategy. Herein, the significant improvements that have recently emerged in the area of the selective activation are discussed. The development of orthogonal strategy further expands the scope of the selective activation methodology. Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences.

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“…Over the years, these and other classes of 2-NHTroc glycosyl donors have been used in glycoside and oligosaccharide synthesis: as trichloroacetimidates, 165,238,258,277, for the synthesis of pyruvated saccharide fragments, 280,304 Lipid A derivatives, 165,281,288,290,294,297,298,305,306 glycopeptides, 277,284,285 lactosaminyl donors, 282,307 Re-type lipopolysaccharides, 289 sialyl Lewis X glycolipids, 291,301 gangliosides, 292 peptidoglycan partial structures, 258,308 thiooligosaccharide analogues 286 of Nod factors, carbohydrate antigens, 295,302 sialyl-trimeric-Lewis X, 300 hyaluronan trisaccharides, 309 meonomycin A analogues, 310 and ceramidated GLA-60 293 derivatives; as fluorides, 282,311,312 for the synthesis of lactosaminyl donors, glycosylamines, 312 and tumor-associated antigen 311 Globo-H; as chlorides; 313 as thioglycosides, 283,286,[314][315][316][317][318][319][320][321][322]…”

Section: Alkoxycarbamoyl Derivatives 2-alkoxycarb-mentioning

confidence: 99%