Participation by C-3 Substituents in Disaccharide Formation

Binkley, Roger W.; Koholic, Dolores J.

doi:10.1080/07328308808058937

Cited by 15 publications

(5 citation statements)

References 11 publications

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“…Although less reactive than the corresponding bromides, deoxy-sugar chlorides are still moisture-sensitive species that must be handled with care . Early reports from Zorbach and Payne on digitoxin monosaccharides indicated that deoxy-sugar chlorides could be directly reacted with nucleophiles to afford glycoconjugates in moderate yield. , Most reports of the use of these donors involve Helferich conditions, − which necessarily require the use of toxic mercury salts.…”

Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural products. Accordingly, there has been sustained interest in methods for their synthesis over the past several decades. The focus of much of this work has been on developing new glycosylation reactions that permit the mild and selective construction of deoxyglycosides. This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter. Where relevant, the application of this chemistry to natural product synthesis will also be described.

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Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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“…Vasella et al 169 recently introduced a new approach to glycoside synthesis using the glycosylidene carbene generated from the diazirine sugar as a novel type of glycosyl donor. The glycosylidene carbene reacted with alcohol in the absence of any additive (Scheme 45).…”

Section: Othersmentioning

confidence: 99%

Recent progress in O-glycosylation methods and its application to natural products synthesis

Toshima¹,

Tatsuta²

1993

Chem. Rev.

1,085

349

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“…A 1,3-acyloxonium or a 1,3-bridging iminium ion was proposed as an intermediate species where the a-face of the donor would be blocked during the glycosylation step ( Figure 9). However, several attempts [93,941 to apply this concept with digitoxosyl halides under silver triflate activation (or thioalkyl digitoxosides under mercury salt activation) showed no reliability in enhancing the P : a ratio of 2-deoxyglycosides.…”

Section: -Deoxyglycosyl Bromides and Fluoridesmentioning

confidence: 99%