An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf

Li, Yao; Yang, You; Yu, Biao

doi:10.1016/j.tetlet.2008.04.017

Cited by 294 publications

(104 citation statements)

References 24 publications

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“…28 The merits of this protocol include: (1) both armed (74) and disarmed (75) glycosyl ortho-alkynylbenzoates could be used as donors; (2) various alcohols (especially hindered ones such as cholesterol, phenol and 4-hydroxyl sugar derivative) could be (3) Au(I) is used catalytically; (4) the yields are generally excellent and specific stereoselectivity could be attained in numerous cases; (5) the reaction condition is mild and orthogonal to other glycosylation protocols. These merits were convincingly exemplified by the efficient total synthesis of the acid labile betulin and betulinic acid derivatives.…”

Section: Gold(i)-catalyzed Glycosylation With Glycosyl Ortho-alkynylbmentioning

confidence: 99%

“…2). 28,[30][31][32] They also discovered that by use of sialyl 2-ortho-hexynylbenzoate 85 as a donor, Ph 3 PAuNTf 2 catalyzed the challenging direct sialylation of various alcohol acceptors in good yields and very high b-stereoselectivity to give the unnatural b-anomers (Scheme 16). 31 Yu et al found unprecedentedly that Au(I) catalyzed the glycosidation reaction of 2-deoxy sugar donors (for example 87) with various primary/ secondary alcohols in nearly quantitative yields and nearly complete a stereoselectivity (Scheme 17).…”

Section: Gold(i)-catalyzed Glycosylation With Glycosyl Ortho-alkynylbmentioning

confidence: 99%

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Chapter 8. Recent advances in gold-catalyzed glycosylation

Luo¹,

Wan²

2014

Carbohydrate Chemistry

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Section: Gold(i)-catalyzed Glycosylation With Glycosyl Ortho-alkynylbmentioning

confidence: 99%

Section: Gold(i)-catalyzed Glycosylation With Glycosyl Ortho-alkynylbmentioning

confidence: 99%

Chapter 8. Recent advances in gold-catalyzed glycosylation

Luo¹,

Wan²

2014

Carbohydrate Chemistry

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“…Use of glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph 3 PAuOTf (Li, et al, 2008g) Hydrangea macrophylla…”

Section: Analysis Of Carbohydrates and Glycoconjugatesmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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“…These include glycosyl bromides, 30 45 and ortho-alkynylbenzoates. 46,47 Listed are also the commonly used promoters for each type of donor, which are demanded by the nature of the leaving groups. Glycosyl phosphates, 48 glycals 49 and pyranones 50,51 have been successfully used in the synthesis of complex glycopeptides 52 and saponins, 53,54 which are not discussed in the present article.…”

Section: Introductionmentioning

confidence: 99%

O-Glycosylation methods in the total synthesis of complex natural glycosides

2015

Self Cite

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The total syntheses of 33 complex natural O-glycosides, such as the glycosides of macrocyclic lactones/lactams, enediynes, angucyclines, and anthracyclines, are highlighted, with a major focus being placed on the O-glycosylation reactions which connect the saccharides and the aglycones. These successful O-glycosylation reactions employ such donors as glycosyl bromides, fluorides, iodides, trichloroacetimidates, N-phenyl trifluoroacetimidates, thioglycosides, sulfoxides, heteroaryl thioglycosides, 1-hydroxyl sugars, 1-O-acetates, and ortho-alkynylbenzoates. Each synthesis is depicted starting from the O-glycosylation of the aglycone (or its precursor); the glycosylation conditions and outcomes (yields and stereoselectivities) are discussed, and the subsequent transformations toward the final target, including the elongation of the glycan, the elaboration of the aglycone, and the protecting group manipulations are also given in detail.

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An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf

Cited by 294 publications

References 24 publications

Chapter 8. Recent advances in gold-catalyzed glycosylation

Chapter 8. Recent advances in gold-catalyzed glycosylation

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

O-Glycosylation methods in the total synthesis of complex natural glycosides

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